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"We are gone to Oregon, it's the greatest family vacation!"
Opening Number
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The result of combining a beloved computer game and one of the funniest acting groups around, The Trail to Oregon is Team StarKid's ninth stage production. The opening scene has the audience name the family (with predictable results). Before the show, the audience use a ballot system to determine which member of the family will die at the end — the mother (Rachael Soglin), father (Jeff Blim), big sister (Jaime Lyn Beatty), little brother (Lauren Lopez), or grandpa (Corey Dorris). Halfway through the show, the audience gets to decide how the family member will meet their demise. This marks the first StarKid show to interact so much with the audience.

The show premiered on YouTube on February 13, 2015. Watch here.

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The Trail To Oregon contains the following tropes:

  • Abduction Is Love: Subverted. McDoon thinks this trope is in effect when he kidnaps the daughter, but it just causes her to lose her attraction to him.
  • Actor Allusion:
    • On the audience's part this time. Many attendees were longtime fans of Team Starkid, so some audience-chosen names included naming Jaime Lyn Beatty's character "Ginevra" or Lauren Lopez's character "Little D" as a reference to the A Very Potter Musical series.
    • There were also direct allusions based on naming the character after the wrong actor for laughs, like naming Grandpa "Jeff Blim" or the Daughter "Brian Holden" (who wasn't even in this show).
    • At the end of the show the Father considers that, since robbing the General Store Guy was much more successful than his career as a farmer, he may take up a life of crime. Both of Jeff Blim's previous major roles for Team Starkid, Sweet Tooth and Aladdin, were sociopathic criminals.
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  • Adaptational Villainy: Difficult as the original Oregon Trail was, at least all the store owners were honest and sold you goods for whatever the market price was at that point in the trail. This show takes the logical Adam Smith Hates Your Guts behavior of the stores raising their prices as you got further along the trail and more desperate and turns it Up to Eleven — this version of the "General Store Guy" won't give you anything close to a fair deal unless you threaten him at gunpoint.
  • The Alleged Car: The Wago-9000 comes equipped with such features as a "floor window" (read: gaping hole in the floor), octagonal wheels (for eight times the traction!), and a blind, toothless ox to pull it. It breaks down no fewer than ten times in the first three months.
  • All Girls Want Bad Boys: The Daughter's reaction to McDoon the Bandit King, at least at first.
  • Ambiguously Jewish: The General Store Guy and his girlfriend both use the Yiddish term scheister (i.e. "shyster") to refer to his questionable business practices. May be Unfortunate Implications.
  • Amusing Injuries: Nearly constantly.
    Son: (stepping directly through the "floor window" of the wagon) Ow! I just broke my ankle!
    Father: (cheerfully) No, you didn't.
    Son : (pouting) Yes I did.
    Father: Don't tell your mother.
  • Anachronism Stew: All over the place, and obviously Played for Laughs. Particularly notable is the gratuitous instance of the General Store Guy passing ownership of his wagon to the Father by giving him the "keys" (especially since there's no prop for the keys and he just says "jingle-jingle").
  • And I Must Scream: Whatever reduced the Ox to his current condition, he isn't happy about it.
    Ox: I'M A MONSTER!
  • And Now You Must Marry Me: In a nod to the constraints on fiction from this time period, the Bandit King seems okay with the idea of drugging The Daughter, abducting her, and holding her prisoner, possibly killing her family in the process, but — at least onstage — he won't lay a hand on her against her will until they're properly married. He may be earnestly waiting for Stockholm Syndrome to set in.
  • Annoying Younger Sibling: The Son to the Daughter. He won't stop messing with her and interrupting her even when they're supposed to be out of character and discussing their own experiences playing Oregon Trail.
  • Artistic License – Biology: At the end of the show the family decides to "buy a cow for that horny ox", which the Ox responds to with "YES, PLEASE!" Even though oxen are, by definition, castrated.
    • Given everything else about the Ox, this is a question probably left unanswered. (Note that immediately after this the Ox peels off his own hide to join the family in their celebratory skinny dipping.)
  • Artistic License – Geography: After passing through the Blue Mountains and rafting the Columbia River, the family arrives at the Oregon state line. The Blue Mountains and the Columbia River are, in fact, within the borders of Oregon. They were stops on the Oregon Trail because the final destination, the Willamette Valley, is in the western part of Oregon. (And to be really technical, the Oregon state line is an anachronism in and of itself since Oregon didn't achieve statehood until 1859 and the musical is said to take place in 1848. In fact, the 1848 borders of the Oregon Territory also included Soda Springs and Fort Hall, both located in present-day Idaho.)
    • At one point the Mother sings "Let's go where the Gold Rush is soaring!", even though the Gold Rush was in northern California, not Oregon (and in fact two-thirds of the male population left Oregon to join in the Gold Rush). Of course, the whole point of the show is this family isn't very well informed.
  • Artistic License – History: In-universe. Grandpa seems to think The War of 1812 was a struggle between the Americans and the lobsters (NOT "lobsterbacks") ending with Grandpa singlehandedly banishing the lobsters back to the sea and being rewarded with a $1 million bill with his own face on it. Later on, he tearfully confesses to the Father that he made all this up... the lobsters were the ones who banished him to the land. This being a Starkid show, it turns out The Cloudcuckoolander Was Right.
  • Artistic License – Medicine: Snakes are venomous, not poisonous — the venom is designed to be injected, and can't survive the acid in the stomach when swallowed. In fact, people mix exotic cocktails with extracted venom in places known for snakes. That said, it's still dangerous to drink snake venom in case you have any open wounds in your mouth or digestive tract where it could enter your bloodstream.
    • "Dysentery World" repeats "Dysentery, dysentery virus" in the chorus. Viral dysentery ("traveler's dysentery" or "stomach flu") is the most common form of dysentery, but is rarely life-threatening in adults. The disease we call "dysentery" that typically killed people on the Oregon Trail was bacillary dysentery, caused by the Shigella bacterium. Of course, any medical information received during a Mushroom Samba hallucination should be taken with a grain of salt.
  • Ate His Gun: The Son literally tries to eat a gun, and unfortunately does it by sticking the muzzle in his mouth with his finger on the trigger. (In his defense, he just told the Mother he experiments with any new object he finds by putting it in his mouth, and she went and handed him a loaded gun anyway.)
  • Attention Deficit... Ooh, Shiny!: The Father, although it's a trait shared by all the male members of the family. May be a Mythology Gag about the seemingly arbitrary things the game has your party leader notice.
    Father: Hey, I found wild fruit!
    Son: Pay attention, dad!
    (later, watching the wagon burn)
    Son: You should've paid attention, dad.
  • Audience Participation: The audience names the characters and decides which member of the family will die.
  • Automaton Horse: Much as in the original Oregon Trail, the family can arbitrarily set the "pace" of their ox-driven cart as though it's a motor vehicle. The ox being fueled with grass is treated exactly like a car running out of gas.
    • Taken to extremes in "Speedrun", where the Mother is somehow able to accelerate an ox-drawn covered wagon fast enough to jump over a river.
  • "Awesome McCool" Name: In the YouTube version, the father gets the name Jack Bauer and is clearly psyched. The rest of the family don't get off so lucky.
  • Ballistic Discount: A delayed variant. When the General Store Guy has his surprise reunion with the Father, he really shouldn't have continued trying to fuck with the guy he initially convinced to go on the trail with no real supplies but a gun and "boxes and boxes of bullets".
  • Be Careful What You Wish For: Lampshaded by the Daughter, who openly wishes for her family to disappear and to be whisked away by the Bandit King, and gets exactly what she wants.
  • Bestiality Is Depraved: The General Store Guy is just a little too insistent there's nothing inappropriate about his relationship with his own ox. The Dikrats themselves joke around about the possibility of being molested by their "horny ox" like it's no big deal, and despite the biological unlikelihood of this (see Artistic License – Biology).
  • Black Comedy:
    • A scene in which the son has to kill a family of buffalo (mom, dad, and baby) is played entirely for laughs.
    • There's also the family's brand new... mutant disfigured ox.
    • The character who is picked to die sings the song "You Gotta Go" while they die painfully of dysentery. It's absolutely hilarious.
  • Book-Ends: The musical begins and ends with the same heroic chords framing the inspiring portrait of an all-American family.
  • Bowdlerization: In the YouTube version, Grandpa's line in "Sometimes It Pays to be an Animal" is "When you wake up with mud on your dick..." The originally written version, which is on the soundtrack, says "blood" instead.
    • Unlike other Starkid shows, this one has an official Bowdlerization available to license for high school productions. This includes cutting off the blasphemous line "God is a vicious two-faced prick" with Dramatic Thunder, replacing the "dick" references in "Sometimes It Pays To Be An Animal" entirely with more backstory between Grandpa and Cornwallis, and turning McDoon and Cletus' relationship from explicit Situational Sexuality to making McDoon Oblivious to Love. (It also includes random edits like directly explaining the "peperony and chease" joke, since most modern high school kids won't have played the original Apple II Oregon Trail.)
    • It's unconfirmed if this was the official bowdlerized script or a change made by their own production, but at least one high school version of this show replaces the song "Naked In A Lake" with its skinny dipping ending with a reprise of "Gone to Oregon", removing any need for the actors to strip to their underwear onstage.
    • There's some controversy over whether, in the YouTube recording of the show, the audience suggestion for the Son's name actually was "Craphole" or if they said "Crackwhore". (As with "blood/mud on your dick", the bowdlerized version is arguably a lot funnier.)
  • Bratty Teenage Daughter: The Daughter is an extremely stereotypical example.
  • Break the Cutie: A Crosses the Line Twice Black Comedy example when the Son is forced to kill the buffalo family.
  • Breathless Non Sequitur: Used a lot in this show as a means of Getting Crap Past the Radar, starting with dropping "Ore-shit" as one of the forced pronunciations of "Oregon" in "Gone to Oregon". In "Independence" Joey Richter uses the breathless pace of the song to throw in casual mentions that one of the hazards of the trail is families giving in to Parental Incest, or note that by participating in Westward Expansion the family is complicit in Native American genocide.
  • Brick Joke: If the audience chooses the ending where the daughter dies, when she revives she does a perfect impersonation of the mother's fake death from earlier. The mother acknowledges how bad it feels to be the victim of the prank.
  • Bumbling Dad: Up to Eleven and initially Played for Laughs but unexpectedly then Played for Drama when the Mother bitterly tells the Father she's leaving him because his incompetence has cost her her daughter.
  • ...But He Sounds Handsome: McDoon approaches the Daughter by pretending to be another random citizen of Independence with advice about the Oregon Trail — in his case, advice about the dashing and dangerous Bandit King.
  • Call-Forward: The Mother sings a snatch of her Award-Bait Song "When the World's at Stake" all the way back in the intro Patter Song "Independence". Later, an instrumental of "When the World's at Stake" plays over her faked death scene, a few minutes before the song proper begins.
    • A very early one for the deathbed song "You Gotta Go".
    Mother: Oh, well, if Grandpa dies that's just God's will. Sorry, Grandpa.
    Grandpa: Oh, that's all right, when you gotta go, you gotta go. You're talking about the shitter, right?
    • In the scene where the Mother fakes her death she says she came back from Heaven because St. Peter told her the Daughter would be "lost without you", which becomes the title of the Daughter's Award-Bait Song.
    • The second time the Son brings up his suggestion to go skinnydipping, he describes it as getting "naked in a lake", and the band actually starts playing the opening bars of "Naked In A Lake" before the Mother cuts it off.
  • Canon Name: The names the audience chose for the performance recorded for YouTube were "canonized" for the official cast recording, with the cast recreating the Audience Participation in "Gone to Oregon".
  • The Cast Showoff: Jeff Blim, who cowrote the show, gives himself an opportunity to come out during the finale number, "Naked in a Lake", to perform a saxophone solo.
  • Catchphrase:
    • The son. "I don't know."
      Mother: How did a bird end up in your mouth?
      [Beat]
      Son: [shrugs] I dunno.
    • "That's what this trip's all about."
    • Not exactly a catch phrase, but the line "Did you just fake your own death?!" is said to lots of different characters.
    • The grandpa says "I'm trying!" quite a few times, and answers questions he doesn't want to answer with "My legs hurt".
    • Grandpa's favorite epithet is "You shicken-kit son of a bitch".
    • "God is a vicious two-faced prick."
    • In direct contrast to the above, the line from "When the World's at Stake", "Lord have mercy on my soul", are both the Mother and Father's Arc Words.
  • Cerebus Syndrome: Even for Team Starkid this show starts out as a Denser and Wackier No Fourth Wall production where the characters barely seem to exist as more than comedic archetypes... until the Mother's song "When the World's at Stake", a completely Played Straight Award-Bait Song about motherhood that caught many viewers off guard. Followed in Act II by the Daughter's song "Lost Without You", even more of a Tear Jerker.
  • Chekhov's Gun: A really out-of-left-field version where the Son's incessant demands to go skinny-dipping leads to the family actually doing so at the ending of the show.
  • Chewbacca Defense: "Sometimes It Pays To Be an Animal" appears to be a philosophical defense of eating meat garbled by Grandpa's senility into Word Salad. It seems to convince the Son through sheer intimidation.
  • Christmas Miracle: We lose track of how far into winter the story has gone until the dead family member suddenly revives, prompting the Son or Daughter to exclaim "It's a Christmas miracle!"
  • Colorblind Casting: Corey Dorris as the grandfather of an otherwise white family.
  • Corpsing: Joey Richter and Jeff Blim suppress laughter when General Store Guy claims he played Tony in West Side Story, which was a Throw It In! on Joey's part.
  • Cutting Off the Branches: The "true" ending of the YouTube version of the show voted on by the original audience was the Son's death. (The other endings were recorded afterwards.) This is the version of the ending that was reenacted for the Very Starkid Reunion show at University of Michigan later that year.
    • The Son Dies ending was the "winner" in terms of being chosen by the audience most often in the original run, possibly because Lauren Lopez is a fan favorite, or because, as the Son himself lampshades when he dies, he was the one most logically likely to get infected.
    Son: I guess I shouldn't have put all that shit in my mouth. Especially that shit .
  • Cycle of Revenge: The reasoning for why, after the Son kills one buffalo, he has to kill the rest of the whole buffalo family. Yes, even the helpless Baby Buffalo, lest he return years later with a team he's put together of buffalo companions.
  • Dawson Casting: Obviously, for the Daughter and the Son, with all the actors being around the same age in Real Life. Interestingly, Playing Gertrude is averted for the Mother — Rachael Soglin seems young for someone who has a teenage daughter, until we find out the Daughter was a Teen Pregnancy.
  • Decomposite Character: The high school version of the play massively decomposes Joey Richter's Loads and Loads of Roles into actual separate bit parts for different actors, since the one thing high school productions can get far more cheaply than professional ones is actors. (In the one production of this script uploaded to YouTube there's even a reference in "When the World's At Stake (Reprise)" to the General Store Guy's Girlfriend having auditioned and failed to play the Daughter.)
  • Derailed Train of Thought: The Father's triumphant return, after the Mother abandoned him, comparing him to a useless pet dog.
    Father: Look, you're right about me, I'm a dog. I'm a dumb, dumb, happy-go-lucky dog. But you know what else a dog is? (clearly expecting the word "loyal")
    Son: Dirty!
    Father: ...More positive.
    Son: Amazing!
  • Deus ex Machina: Cornwallis, the leader of the lobsters, saves the family from drowning and slips Grandpa's million dollar bill from the War of 1812 back into his pocket, which is enough money to instantly solve all of the family's problems once they reach Oregon.
  • Dirty Coward: The Father, aside from general ditziness, is a bit of an Extreme Doormat, as seen when the General Store Guy takes him for a ride on the Wago-9000. This leads to his greatest failure when the Bandit King comes for the Daughter and, as the Mother says when she leaves him, he "didn't even fight back". He finally sheds this trait when, after having lost everything, he runs into the General Store Guy again.
  • Disney Death: The family member that dies of dysentery gets revived minutes later after their body is dragged across the border into Oregon.
  • The Ditz: The Father and Grandpa (though Grandpa does have a The Cloudcuckoolander Was Right moment at the end). The son also has shades of this, but he is only seven years old (apparently).
  • Double Entendre: Many throughout the show, but the most notable is the secondary meaning of McDoon telling Mouthface he wants to "Caulk Your Wagon".
    McDoon: (slathering caulk over the wagon) Let me fill your holes...
    • The lyrics of "You Gotta Go" are an incessant barrage of Toilet Humor double entendres.
  • The Eleven O'Clock Number: A hilarious deconstruction of this trope, where the penultimate number is an extremely heartfelt and dramatic Death Song that any of the family members might get as a solo depending on the audience's vote — a death that happens completely arbitrarily before the show ends, that is then undone just as arbitrarily, and that is just one long fart/poop joke.
  • Everyone Calls Him "Barkeep": The general store guy's ladyfriend calls him General Store Guy.
  • Everything Trying to Kill You: The basic nature of Oregon Trail, and the main theme of "Independence".
    Stay away from Old Man Bridger
    When he's drunk he'll take your liver
    Life is not a petting zoo
    Or you'll get ripped in two
    (pant, pant)
    BY A BEAR! OR A SNAKE!
    Mother Nature's really great!
    Staying alive can be lots of fun!
    Be sure you have a loaded gun!
    Something will go wrong!
    The list is far too long!
    Declare your independence!
  • Excited Show Title!: The Trail to Oregon!
  • Excuse Plot: The whole story, since it's based on a video game. But especially the subplot with McDoon kidnapping The Daughter, where it seems he has to follow the Oregon Trail to its end even though his stated goal is to take her to Mexico. It would make more sense for him to branch off onto the California Trail or Mormon Trail if he plans to eventually go south — but, after all, that wasn't an option until Oregon Trail II.
  • Extreme Omnivore: The son; if he doesn't know what an object is, he will try to eat it. This includes a scorpion, a dead bird, and a gun.
  • The Faceless: Darla the barmaid and the General Store Guy's girlfriend both wear bonnets tied tightly enough to hide their eyes from the audience, to avoid distracting the audience with the fact that they're played by the same person as the missing Daughter.
  • Fake Interactivity: Zig-zagged. The audience genuinely does get to name the family members and decide which one dies at the end; however, the claim that they get to choose what disease the character dies from is made under the assumption that the audience will always say dysentery, the fan-favorite from the game.
    • Along the same lines, the introduction implies you'll be able to choose the family's profession like in the game only for the Father to go ahead and just declare that they're farmers, basically forcing them to play on Harder Than Hard difficulty (much to the Mother's chagrin).
    • For the New York run of the show, the voting for who dies in the end was rigged to make sure every actor would get a roughly even number of turns to sing "You Gotta Go". (Having everyone have to rehearse this song knowing that some of them might rarely or never get to perform it was one of the more burdensome aspects of this show's interactivity.) This was also the run where Joey Richter got A Day in the Limelight with the "Ox Dies" ending.
    • As is common in any stage show that relies on Audience Participation, it's been revealed that the audience had plants each night who would yell out prearranged names just in case none of the real audience suggestions were usable, combined with a few cases of strategically mishearing suggestions that might have been distractingly offensive.
  • Faking the Dead: The mother does this while guilt-tripping the daughter; apparently, she did it quite often in the past. She pulls the same stunt if she's the one who "dies" of dysentery. If the daughter is chosen to die, she does this in order to get back at the mother. The mother begrudgingly promises to never do it again.
  • First Town: Independence, MO. Most of the associated tropes are lampshaded in the eponymous song.
  • Foreshadowing: "Independence" is packed with it, although mixed with plentiful Red Herrings.
  • Former Teen Rebel: The Mother is presented as a strict, conservative foil to the Father's goofy Bumbling Dad — but then "When the World's at Stake" reveals that she used to be a dancer in saloons and a gambler who accumulated debts, before she got pregnant with the Daughter and her life was derailed. Includes surprisingly Played for Drama details like that she seriously considered getting an illegal abortion.
  • Friend to All Living Things: The Son, which makes the Mother's decision to send him out hunting unfortunate.
  • From the Mouths of Babes: The Son's parting speech with the Father when the Mother leaves him about how much he also hates being "in trouble with Mom" seems like a total Non Sequitur, but it seems to spur the Father into action when he realizes he's been more worried about being "in trouble" and keeping people happy, like a child would, than actually thinking about the practical consequences of his actions, like an adult. This inspires him to redeem himself by confronting the General Store Guy who swindled him and taking what he needs from him at gunpoint.
  • Funny Background Event: Listen carefully during "Gone To Oregon" in the recorded version of the show and you'll hear an audience member shouting "GAYLORD" with increasing desperation as the cast asks for names.
    • During the extremely dramatic confrontation between the Mother and Father at the Fort Bridger tavern, the Son quietly collects and drinks everyone else's abandoned Mike's Hard Lemonades. Despite the Bartender's warning about their negligible alcohol content, this seems to be enough to get him quite tipsy by the time he delivers his parting words to the Father.
  • Fun with Subtitles: Joe Walker contributed the English subtitles for the YouTube version of the show, throwing in fun asides like subtitling the reaction to a joke about Wisconsin as "(People in the audience ostensibly from Wisconsin cheer)". He especially had fun with Purple Prose descriptions of the fart sound effects in "You Gotta Go".
  • Golden Ending: Crossed with a "Joke Ending". Legend has it there's a special ending where all the human characters survive and the Ox is the one who dies of dysentery, that was only performed once.
    • According to reports from those who've seen it, the "Ox Dies" ending is essentially A Day in the Limelight for Joey Richter, giving him the same chance everyone else had to perform "You Gotta Go". It also included allowing the General Store Guy to finish singing "When the World's at Stake", gives the Ox an Alas, Poor Scrappy death scene where he asks the family to carry a letter to his estranged daughter, and has him give a Dying Declaration of Love and Last Kiss... not to the Daughter, but the Son. (As disturbing as the implications of kissing a seven-year-old boy might be, this is clearly throwing a bone to real life Richpez shippers.)
  • Grief Song: "Lost Without You" is a very pure, sincere Award-Bait Song for the Daughter.
  • Happy Ending: We're naked in a lake!
  • Harder Than Hard: This show repeatedly makes fun of how, of the three professions in the original Oregon Trail, being a farmer was essentially hard mode, starting with little money and no useful skills. (They're also a family of five, the maximum number of party members in Oregon Trail — this also does nothing but increase the difficulty of the game, lampshaded by pretty much everyone but the Mother being The Load most of the time.)
  • Hero of Another Story: In the livestream version of the show, the General Store Guy ends his confrontation with the Father by mentioning he plans to workshop his own version of the show at the Independence Fringe Festival, entitled "Wagons, Whiskey and Women: A General Store Guy's Story", or possibly just "How to Succeed in Business Without Really Trying".
    General Store Guy: It's gonna start with this number where I'm in the General Store and I'm like "I gotta sell things", and this family comes in and I just totally fuck 'em over! It's gonna be great.
  • Historical-Domain Character: None appear onstage, but a few are mentioned, such as then-current President Polk, whom the Mother would play as when she played Oregon Trail or former President Martin van Buren, whom Grandpa apparently used to go skinny-dipping with. It's unclear whether the lobster leader Cornwallis from Grandpa's stories is supposed to be the same person as British Revolutionary War General Cornwallis or if he just had the same name. He does turn out to be real, though.
  • Historical In-Joke: The line "Stay away from Old Man Bridger" in "Independence".
  • Honest John's Dealership: The General Store.
  • Hypocritical Humor
    Mother: Did you just fake your own death? What kind of parent are you?!
    • Also, the Mother constantly tears into the Father for being a Bumbling Dad, but even at his worst he doesn't do anything as bad as handing a seven-year-old boy a loaded gun and telling him to "figure it out".
  • I Just Want My Beloved to Be Happy: Cletus Jones' stated reason for not helping the Daughter escape McDoon's clutches.
    Cletus: You may be a homewrecker, but I'm not.
  • Improv: Joey Richter would improvise a line every night to react to his failure to hit the high note in the General Store Guy's duet/confrontation with the Father, referencing the General Store Guy's musical theatre career back in Independence. The Audience Participation also gave many opportunities to improv jokes around the characters' names.
  • Informed Ability: In-universe. The Father tells the General Store Guy that as a farmer he has the necessary skills to "live off the land". He demonstrates no such skills at any point. True to the original Oregon Trail, where being a farmer simply meant you started with the least amount of money (although later editions of the game averted this).
  • Insane Troll Logic: According to Grampa, the devil carries pitchforks, and farmers carry pitchforks. Ergo, farmers are the devil.
  • Ironic Echo: If the Son dies, he repeats the Mother's comforting words from when he killed the baby buffalo.
    Son: It's all right. I'm going to Heaven now. Or maybe I don't have a soul. Either way, it was God's will.
  • It Is Pronounced Tropay: It's a bit of a Shibboleth for people who live in Oregon that the proper pronunciation of last syllable of "Oregon" is pronounced "gun", NOT "gone". Perhaps riffing on this, the opening song "Gone to Oregon" defiantly rhymes "Oregon" with "gone", then keeps changing the last syllable of "Oregon" to match the rhyme of the previous line ("Ore-goon", "Ore-gap", "Ore-shit".)
  • It Will Never Catch On: During "The Grind", the Father wishes there were such a thing as a portable handheld camera to take snapshots with (in the ongoing parallel with National Lampoon's Vacation). Photography did exist in this time period, but was far more expensive and cumbersome.
    Father:I wish there was something that could capture this moment
    Something that fits right into your pocket
    But we got time to kick the idea around
  • Knight of Cerebus: The Bandit King himself is a pretty silly character, but the fact of him kidnapping the Daughter is very much Played for Drama.
    Bandit King: YOUR WAGON IS ON FIRE!
  • Know-Nothing Know-It-All: The Father tries to bluff the General Store Guy about his knowledge of the trail. This backfires and inspires the General Store Guy to take him for all he's got .
    General Store Guy: No food?! Okay, suit yourself, if you wanna end up like the Donner Party .
    Father: The Donner Party? They knew how to have a good time! You hear that, kids, we're gonna be just like them!
  • Legacy Character: Played with. It's hinted that the Father might take up McDoon's legacy as the Bandit King, since robbing the General Store Guy has been far more successful than any of his attempts at farming. Becomes moot thanks to Grandpa's fortune.
  • Let's Get Dangerous!: When the Father decides to get back what the General Store Guy swindled from him at gunpoint.
  • Loads and Loads of Roles: Joey Richter as "Everyone Else" outside the main family, i.e. all of the Non Player Characters of the game. Essentially the Game Master of this story.
  • Lost Lenore: Grandpa's long-lost wife, Eleanor. (Which is even what "Lenore" is short for.)
  • Made of Incendium: Among all the other shortcomings of the Wago-9000, apparently a single stray cigarette is enough to make it immediately go up in flames.
  • Mama Bear: The Mother. Like woah.
    Mother: (to the Bandit King) You see that girl right there? I made her. Out of my blood and my flesh, my sweat and my tears. And I love her more than the wakin' world. But I will smother her in her sleep before I see her ruin herself with some thing like you, so you better just run along now cause you'd have better luck sticking your pecker in a cactus.
  • Manchild: The Father, in spades. Lampshaded in the Son's death.
    Son: Goodbye, Dad. Looks like you're Mom's only son now.
    Father: No, you're Mom's son, I'm the father, remember?
    Son: Right. The father. The oldest son.
  • Massive Multiplayer Ensemble Number: The ending of "Wagon on Fire". Also a minor Reprise Medley (and a Dark Reprise) of "The Grind", "When the World's at Stake" and "Gone to Oregon", with "Sometimes It Pays to Be an Animal" thrown in as a joke.
  • Meaningful Name: "Independence" happens to be both the real life starting point for the Oregon Trail (Independence, MO) and the thing the people on the trail are seeking.
    • The fact that the Son happened to be named "Craphole" in the YouTube version of the show may have played a role in the audience choosing him to die of dysentery that night.
    • Audiences named the Daughter "Mistake" or "Mishap" multiple times, possibly because the audience member in question had seen the show and knew about the Teen Pregnancy backstory. (Perhaps riffing on this further, one audience named the Son "Adopted" in order to add backstory.)
    • Naming the Father "Jack Bauer" was not only appropriate given his violent rampage to get his daughter back, it's also a (probably unintentional) Stealth Pun, since "Bauer" means "farmer" in German.
  • Memetic Hand Gesture: Everyone crosses their face with an ominous two fingered hand gesture when they say the phrase "the Bandit King", including the Bandit King. This leads to his Surprisingly Sudden Death.
  • Mood Whiplash: All over the place, in a show even Denser and Wackier than usual for Starkid. Special mention goes to the heartwrenching sight of the Mother pulling off her wedding ring to trade it to the Bartender for a bottle of whiskey — and the Bartender mistaking this for a marriage proposal.
    • One major draw of this show is how the cast commits to using the audience's selected names even during dramatic, serious scenes, for the same Mood Dissonance humor as when you pick a joke name in a video game. (E.g. in the YouTube version, when the Daughter calls herself "Mouthface" in the middle of her big Award-Bait Song "Lost Without You".)
  • Multiple Endings: Played with. Anyone Can Die based on the audience's votes, but this is always a Disney Death and leads to the same ending, "Naked In A Lake".
    • There's also an actual Revised Ending for the high school version of the play, where instead of joyous skinny dipping the family gets a slightly Downer Ending of meeting their Always Someone Better counterparts in a reprise of "Gone to Oregon".
  • Mushroom Samba: "Dysentary World", a hallucination the father has while dying from snake venom, complete with the other cast members dancing around in animal masks.
  • Musicalis Interruptus: The Son interrupts the Dad when he gets carried around in his singing and dancing solo in "The Grind".
  • Mythology Gag: In the filmed version the audience gives the family the last name Starkid spelled backwards: Dikrats. (This name was first referenced in the 2012 Apocalyptour.)
    • The show has many references to Memetic Mutations from Oregon Trail: dying of dysentery, a tombstone reading "peperony and chease", "Friends don't let friends ford the river". There's also a few references to the later, lesser known graphical adaptations of Oregon Trail, like the Bartender telling the barmaid Darla "You've been polishing that same glass for two weeks".
    • The Mother's suggestion to McDoon to "stick your pecker in a cactus" is the same ultimate punishment for a penis Weenie used on Dick in Me and My Dick.
    • The plush snake toy that "bites" the Mother's leg in her sleeping bag is the same prop as the snake that bit Snape on the wiener all the way back in A Very Potter Musical six years prior (i.e. the Team Starkid version of Nagini).
  • Named by the Adaptation: Inverted. The General Store Guy is just "General Store Guy" even though the owner of the Independence general store in the original Apple II Oregon Trail was named "Matt".
  • Nay-Theist: As is tradition for Starkid, the script is over-the-top anti-religious, to the point that "God is a vicious two-faced prick" is the Father's catchphrase. A bit deeper than usual though, since this is part of the Father's Never My Fault immaturity and also a commentary on the Everything Trying to Kill You nature of the original Oregon Trail. (And the Mother does get some surprisingly sincere moments of prayer to God in her private moments.)
  • Neoclassical Punk Zydeco Rockabilly: The music in the show is a fusion of the Broadway show tunes you'd expect from a stage show, Western-style music you'd expect from the setting, and funk of all things.
  • No Fourth Wall: To an extreme degree even for a Starkid show, especially during the opening "Gone to Oregon" number. The concept of the audience naming the characters is introduced by the actors, out of character, reminiscing on how they picked names when playing the game as children. When the Mother asks why the Father (played by Jeff Blim) gets to choose their starting profession he cheerfully replies it's because he wrote the script. The song goes on to excuse any Black Comedy or Artistic License – History by reminding us it's not even based on the historical Oregon Trail but the computer game.
    Chorus: It's only a game
    I guess it's only a game
    The Trail to Oregon is nothing but a game
  • Not Quite Back to Normal: Ditzy as the Father is normally, he still seems to be a little bit off after his miraculous recovery from his Mushroom Samba experience with snake venom in "Dysentery World".
    Father: Of course I am, honey.
  • Not So Different: The General Store Guy to the father, when he (attempts to) sing his part of "When the World's at Stake." Despite being a fast-talking conman, he is shown to be willing to do absolutely anything to save his lady friend/wife.
  • Off the Wagon: We learn in Act 2 that the Mother had a drinking problem inherited from her wild youth before the Father got her pregnant, and has been on the wagon for years until she falls off the wagon because the wagon burned down.
  • Old-Timey Ankle Taboo: When the Mother tries to incite the Father to "woo" her, she does so by seductively sticking her ankle out from her dress.
  • One Last Job: McDoon announces that watching the family struggle and sacrifice for each other has inspired him to become a Retired Outlaw after One Last Job. Unfortunately, that last job is kidnapping their daughter and forcing her to marry him so he, too, can start a family.
  • Only Sane Man: The Mother, as is typical of sitcom moms. The whole rest of the family take turns being the Cloud Cuckoolander and The Load (although the Daughter joins in more as a Troll).
    Mother: (as the rest of the family joins the Father in flapping their arms to try to fly) Well, if you can't beat 'em, join 'em. Luckily, I can beat' em. (proceeds to slap each of the family members one by one)
  • Parental Favoritism: Inverted. When The Daughter thinks her mother has died, her immediate reaction is to scream at God, "WHY COULDN'T YOU HAVE TAKEN DAD INSTEAD?!"
  • Parents as People: The point of "When the World's at Stake".
  • Patter Song: Most of Grandpa's verses of "Pays to be an Animal", combined with Word Salad Lyrics. Same with "Independence", sung by Joey Richter as, apparently, the entire population of Independence, Missouri.
  • Playing Hard to Get: The Mother angrily rejecting the Father's sexual overtures turns out to be this. McDoon seems to think the Daughter struggling to escape from being kidnapped is this.
  • Product Placement: Mike's Hard Lemonade. Just to make fun of it, of course.
  • Purely Aesthetic Era: The play is naturally overloaded with humorous anachronisms, such as General Store Guy mentioning that he acted in West Side Story.
  • Rage Against the Heavens: A Breaking the Fourth Wall version where thanks to his venom-induced vision in "Dysentery World" the Father becomes aware of the "Watchers", metaphysical entities visiting misery on his family for their own sick amusement (i.e. the audience).
  • Real After All: The appearance of Joey Richter as Cornwallis the Lobster King is one of the most memorable such reveals in Starkid history, beating out Jim Povolo as Rumbleroar in A Very Potter Musical.
  • Reprise Medley: Much of "Wagon on Fire" consists of the family singing snippets of previous songs. Spoofed at the end, when the son sings the "mud on your dick" line from "Pays to be an Animal".
  • Run for the Border: The show treats the "Oregon state line" like a literal magical threshold that will fix everyone's problems when they cross it. In a more realistic example, McDoon plans to retire from his bandit career by taking his new child bride with him down to Mexico.
  • Scare Chord: Plays whenever it's mentioned that one of the family members is doomed to die of dysentery. Also plays when the Bartender fails to get rid of his last bottle of Mike's Hard Lemonade.
  • Secret Identity: Mr. McDoon is The Dreaded Bandit King. Although he isn't particularly careful about keeping his secret. And his minion Cletus Jones even less so.
    Cletus Jones: Don't you shush me! I just got back with all your supplies... firearms, ether, bandit masks...
  • Self-Deprecation:
    We're Broadway-bound
    In Ore-gound
    'Cause there's no Broadway in Chicago
    You could go next door and see something professional
    We wouldn't blame you a bit
    Over sitting through this Ore-shit
  • "Shaggy Dog" Story: Lampshaded in the ending where the daughter dies. The family just spent the second act of the musical looking for her and finally rescued her, only for her to suddenly die of dysentery. It's played for laughs though.
  • Shotgun Wedding: In a moment of brutal honesty the Mother reveals in "When the World's at Stake" that she wasn't in love with the Father when they got married but went ahead with it because she was scared of being a single mom.
  • Shout-Out: Numerous elements, like the quality of the family's wagon and the Father's Catchphrase "That's what this trip's all about!", allude to National Lampoon's Vacation.
    • Given Team Starkid's well known love for the Sam Raimi Spider-Man Trilogy, Grandpa's cold "This doesn't change anything" to Cornwallis after he saves his life is probably a reference to Harry Osbourne saying the same to Spider-Man in Spider-Man 2.
    • The song "Caulk Your Wagon" is both a reference to the famous "caulk the wagon and float it" option for crossing the river in Oregon Trail and a parody of the song "I'm On My Way" from Paint Your Wagon.
  • Significant Double Casting: At the opening of Act II, when the Daughter has been kidnapped by the Bandit King to be his bride, Jaime Lyn Beatty also shows up as the female companion of two of Joey Richter's other characters (the Bartender and the General Store Guy).
    • The Father Buffalo and Mother Buffalo are played by the same people as the human Father and Mother, though this may be a result of the Son hallucinating.
  • Situational Sexuality: McDoon sees his relationship with Cletus Jones this way, and is eager to stop "messing around" and settle down with a real woman (well, teenage girl). Cletus is not so eager, but in the end accommodating.
  • Slasher Smile: A staple of Jeff Blim's performances as Aragog, Sweet Tooth and Aladdin, it makes an unexpected return when the Father unexpectedly pulls a gun on the General Store Guy.
  • Slow Motion: Hilariously simulated to demonstrate the wagon's improbable speed in "Speed Run".
  • Speech Impediment: Rachael Soglin plays the Mother with a noticeable lisp.
  • Speed Run: In the song "Speedrun", after the daughter gets kidnapped by Mc Doon, the mother uses this trope to catch up, even referring to the game mechanics for such a thing — "We're setting our rations to Bare Bones and our pace to Grueling!" — and saying "We're gonna do... a Speed Run!"
  • Stockholm Syndrome: Played with. The Daughter never actually stops trying to escape from McDoon or resist his advances, but after he dies she calls him "the love of her life". (Though she may just be trying to get a rise out of the Mother.)
  • Stylistic Suck: The General Store Guy tries to get in on the Father's reprise of "When the World's at Stake" only to suffer Inopportune Voice Cracking. While they try to make this look like a real Vocal Range Exceeded on Joey Richter's part (complete with a Throw It In! line to play it off) Starkid fans who've seen him sing in other shows know that it isn't.
  • Tag Along Kid: The Son combines most of the tropes associated with this kind of character, including being a Bratty Half-Pint Annoying Younger Sibling to the Daughter and being The Millstone to his parents.
    Son: I don't know why I throw supplies off the back of the wagon... It just happens.
  • Take That!: Apparently Mike's Hard Lemonade really sucks.
  • Take That, Audience!: If the audience chooses to kill the daughter or son, the mother asks rhetorically what sort of heartless person would choose to kill one of the children.
  • Teen Pregnancy: The Mother got pregnant with the Daughter at 17 and seeks to avoid history repeating.
  • The Promised Land: Oregon.
  • "The Reason You Suck" Speech: The Mother gives a devastating one to the Father before she leaves him.
  • Time Passes Montage: A version of this based on Reading the Stage Directions Out Loud, where the passage of days is marked by raising and dimming the stage lights while Joey Richter as the Ox says "Cricket, cricket" or "Cock-a-doodle-doo!" while still doing the Ox's strained, distorted voice.
  • Toilet Humour: When a family member dies of dysentery, Dr. Joey Richter provides some impressive sound effects as the unfortunate victim flops around on the ground.
  • Too Much Information: Jeff Blim's reaction when Lauren Lopez "breaks character" (not really) to discuss what she named her own Oregon Trail characters as a kid.
    Son: I think I would use my mom and dad's names of course
    So I'd make sure they'd never get divorced!
    Father: That might be too much information
    But hey! It's great to have that personal connection!
  • Triumphant Reprise: "When the World's At Stake", which first appears as the Mother's reflection on how much she's sacrificed for her family, and which comes back as the Father deciding to finally man up and do the same by robbing the General Store Guy. Then immediately parodied, with the General Store Guy hijacking the song to declare how from his POV he's the hero for giving in to the Father's demands to save his girlfriend from getting shot. (Then subverted, by having the not-truly-heroic General Store Guy utterly fail to hit the heroic high note.)
  • Unfortunate Names: Let the audience name your characters, and you'll end up with these. A father called Dickweed, a mother called Lily Pad, a daughter called Dysentery, a son called Chlamydia, and the grandfather, Master Roshi.
    • And yes, the daughter's name in such productions is endlessly lampshaded.
      Doctor: One of you has Dysentery!
      (Various family members): Oh yeah! She's right here! etc.
      Dysentery: Please don't take me away!
      Doctor: What?
      Family member: Her name is Dysentery.
      Doctor: Oh. That's... unfortunate.
    • And later...
      Grandpa: I'm dying of Dysentery!
      Dysentery: Oh, I'm so sorry Grandpa
    • In one version, the daughter is named Dad. Imagine how confusing that was.
    • In the YouTube version, the father is named Jack Bauer, the mother is named Slippery When Wet, the daughter is Mouth Face, the son is Crap Hole, and the grandfather is Titty Mitty. The family name, meanwhile, is Starkid spelled backwards... which, as it turns out, is Dikrats. Yikes.
  • Unknown Rival: The high school version of the show suddenly reminds us this is a video game with the "Gone to Oregon (Reprise)" ending, where the family meets the Always Someone Better version of themselves — who, by using their resources more wisely, were able to take the Barlow Toll Road rather than the Columbia River crossing (one of the most notorious Cash Gate Easy Mode choices in early gaming) and avoid all of the complications of the play. As a result, despite the Mother's actions in "Speed Run", they've beaten the family's travel time (which is what the game used for a scoring system) and have taken the tract of land the family wanted, refusing to sell to them despite their newfound wealth. The ending implies a Here We Go Again! story about the drama between the family and their new neighbors, rather than the Golden Ending of the original.
    • Ironically this makes the song "Independence" Hilarious in Hindsight with the one piece of advice the family did heed, "Don't pay the toll, not worth the cost", tragically mistaken.
  • Unwitting Instigator of Doom: The YouTube descriptions for the ending videos of the show tell us that whichever family member gets dysentery is the victim of McDoon's posthumous revenge, since they contracted it as a result of him "taking a dump in the great Columbia River" just before they were immersed in it.
  • Villain Song: "Wagon on Fire" for the Bandit King. Hilariously, it lampshades the difficulty of carrying out an evil plan while also singing about it by having Cletus Jones do most of the actual villainy.
    Bandit King: Grab her, bag her, whatever you want
    I'm too busy saying what's going on
  • Vocal Range Exceeded: Played for Laughs when General Store Guy tries to hit a high note in "When The World's At Stake".
  • Wedding Ring Removal: Judges and courthouses are in short supply along the Oregon Trail, but the Mother makes it pretty clear she considers selling her wedding ring for a bottle of whiskey the next best thing to a formal divorce.
  • What Did I Do Last Night?: Grandpa's Fauxlosophic Narration about being Not So Different from animals in "Sometimes It Pays To Be An Animal" takes a Shocking Swerve into a garbled description of literally waking up as an animal mixed up with an actual What Did I Do Last Night? Bedmate Reveal from Grandpa's hilariously checkered Mysterious Past. And given everything we eventually learn, the whole thing might even somehow be literally true.
  • What the Hell Is That Accent?: The Bartender's (and his barmaid, Darla's) vaguely Scandinavian-sounding accent, which mostly serves to distinguish them from the General Store Guy and his girlfriend who show up in the same scene.
  • Writing Around Trademarks: Played with, as is traditional for Team Starkid — the name "The Trail to Oregon!" itself is a Paper-Thin Disguise for The Oregon Trail, but the show is careful to never actually say "Oregon Trail" to refer to itself (while freely using that name for the actual Oregon Trail).
  • You Bastard!: If either the son or daughter are selected as the one who dies, the mother wonders what kind of person, if given the choice of which family member had to die, would choose one of the children. If it's the daughter, the father further muses about how there's no way anyone could find this situation funny.
  • Zillion-Dollar Bill: Grandpa was literally given a million dollar bill with his own face on it for his services driving lobsters into the sea during the War of 1812 (the details are obscure). For reference, $1 million in 1848, when the musical was set, would be roughly $30 million in 2015 dollars.

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