ALL SPOILERS ARE UNMARKED. You have been warned.
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Scott Thomas
Scott Thomas
Played by: Scott Mechlowicz
A teenager who wanted to talk to his pen pal.
- Actually Quite Catchy: Though the first time hearing it was incredibly traumatizing for Scotty, he later admits that the song Scotty Doesn't Know (in which the singer goes into great detail about how Fiona cheated on Scotty with him) is pretty catchy.
- Jerkass Ball: Invoked due the Placebo Effect he and Jenny had when eating a plate of brownies, mistakenly thinking those are hash brownies. Outside of this they are actually pretty decent people.
- My Hovercraft Is Full of Eels: Scott's German is quite poor, to the point that he doesn't realise that Mieke was a girl all along despite the fact that he's been emailing her for quite a while. There's also his conversations with the truck driver while trying to hitch a ride to Berlin, not realising that the driver is going as far away from Berlin as possible.
Cooper Harris
Cooper Harris
Played by: Jacob Pitts.
"This isn't where I parked my car."
Scott's best friend.
- Amusing Injuries: Cooper getting brutally sodomized and having his testicles electrocuted. If this weren't a comedy, he'd probably be traumatized for life.
- Breaking the Fourth Wall: While peeking through the bushes at the topless women in the hot tub at the post-graduation party, Cooper comments, "Well there's your R-rating right there", at which point the scene cuts to a clear shot of one of the aforementioned women.
- Character Catchphrase: "This isn't where I parked my car."
- Jerk with a Heart of Gold: Coop may be a snarky, perverted slacker, but he loves his friends. He even gives Jamie a big bear hug when they part ways.
- Sex Tourism: Cooper's main purpose with the trip.
- "Ugly American" Stereotype: Coop fits the bill more than the rest of the gang. He's looking to score with hot European women with absolutely nothing else on his mind. His antics at the Vatican further hammer across his uncultured ways.
Jenny
Jenny
Played by Michelle Trachtenberg.
- Jerkass: Invoked due the Placebo Effect she and Scott had when eating a plate of brownies, mistakenly thinking those are hash brownies. Outside of this they are actually pretty decent people.
- One of the Boys: Jenny in the beginning is regarded by Cooper as not a girl, instead being "just a cool guy with long hair".
- Which can be a headscratcher especially considering that Jenny was never shown at any point in time to be dressing unattractively for a pervert like Cooper to completely dismiss her though it might just be that he grew up with her
- More likely the fact that he respects her (when he habitually objectifies all other women) makes her an "honorary man" in his eyes
- Toplessness from the Back: In the extended deleted scene with the gang trying to hitch a ride to Berlin, Jenny partially flaishes by lifting her shirt, which because she's wearing a bra is shown from the front. When she takes the bra-and eventually her shirt-off though, the camera cuts to behind her and it stays that way as she's jumping topless and lassoing the shirt. If Michelle Trachtenberg had her 18th birthday before the scene's filming, this would likely have been averted.
- Twincest: She kissed her twin brother after drinking absinthe.
Jamie
Jamie
Played by Travis Wester.
- Big Brother Instinct: Very protective of Jenny, objecting to any plan to use her as Ms. Fanservice.
- Camera Fiend: He doesn't go anywhere without his trusty Leica M7.
- Distracted by the Sexy: Jamie gets robbed at knife-point in Amsterdam, but he's too busy getting a blowjob from a local girl to put up much of a fight.
- Karmic Jackpot: Jamie selling his camera to take Scotty to Rome to see Mieke. It starts a series of events that ends with him getting hired to tour all of Europe's museums.
- Twincest: He kissed his twin sister after drinking absinthe.
Fiona
Fiona
Played by Kristin Kreuk
Scott's high school sweetheart, who has been cheating on him for a full year before graduation.
- All Girls Want Bad Boys: Fiona cheats on mild-mannered, middle-class Scott with the lead singer in a rock band.
- It's Not You, It's Me: Although, seconds later, Fiona retracts this and insist that it is in-fact Scotty's fault. Considering it's a Minor Flaw, Major Breakup, her claim is debatable.
Donny
Donny
Played by Matt Damon.
"This one's for you, baby. Happy anniversary."
A rocker who admits that Scotty had his girlfriend cheat on him... with him.
- The Cameo: He only appears in the prologue.
- Refuge in Audacity: Fiona and Donny don't just tell Scotty that they've been having an affair. He writes and performs with his band a full song (at the graduation party, no less) all about their affair and various sex acts, all to the refrain of Scotty (who is in the audience) not knowing anything.
- Small Role, Big Impact: His song "Scotty Doesn't Know" has become so popular that the song becomes a part of the plot.
Mad Maynard
Mad Maynard
Played by: Vinnie Jones
A passionate fan of Manchester United FC who befriends Scotty and Cooper in London.
- Berserk Button: He really hates Italians.
- Face of a Thug: He's very intimidating looking, but he turns out to be a rather nice fellow.
- Football Hooligans: He and his buddies are ready to get into a fight over another person wearing a rival club's shirt.
- Hard Head: Maynard gets unaffected by bottles being broken against his head.
- Hidden Depths: Appears to have quite a good understanding of the European political situation and the need for the EU.
Robot Man
Robot Man
Played by: J. P. Manoux
A French street performer that gets into an altercation with Scott.
- Green-Eyed Monster: He's clearly jealous that Scott's robot impression is more popular than his own.
Creepy Italian Guy
Creepy Italian Guy
Played by: Fred Armisen
"Mi scusi!"
A perverted commuter with a taste for unassuming teenage boys.
- Black Comedy Rape: Scott wakes up from a very pleasant sex dream involving Mieke, only to find the Creepy Italian snuggling up next to him in the exact same position he dreamed Mieke was in. Cue everyone screaming.
- Catchphrase: Mi scusi.
- Depraved Homosexual: He doesn't take "no" for an answer.
- Faux Affably Evil: He plays off every blatant advance he makes on Jamie and Scott as innocently as possible...only to make even more invasive comeons seconds later.
Madame Vandersexxx
Madame Vandersexxx
Played by: Lucy Lawless
The owner of Club Vandersexxx in Amsterdam where clients receive pleasure beyond their wildest dreams.
- Dominatrix: The actual purpose of the club is to give BDSM services to the clients, much to Cooper's horror.
Absinthe Fairy
Absinthe Fairy
Played by: Steve Hytner.
"I'm not feeling a goddamn thing. This absinthe is bullshit!"
A green fairy that appears after the men drink absinthe.
- Advertised Extra: He appears in every part of marketing but only appears in two scenes of the film.
- Bowdlerise: In the trailer, he says "That is just wrong" instead of "That is some pretty fucked up shit."
- Catchphrase: "This [X] is bullshit!"
- Fairy Companion: Downplayed. He only appears in hallucinations.
- No Name Given: We don't even know his name.
- Screw This, I'm Outta Here: He says the last three words verbatim as another catchphrase.
- Sir Swears-a-Lot: He is a sweary fairy and swears in nearly every sentence he says.
Mieke
Mieke
Played by: Jessica Boehrs
Scott's German pen pal.
- All There in the Script: Mieke's last name is revealed as "Schmidt", as shown in a scene where Scotty tries to reply back to her after she blocked his e-mail address, and in a deleted scene, where they meet the Creepy Italian Guy, who is the supervisor for a touring company in the Vatican City.
- Gender-Blender Name: Scott initially assumes she's a man due to pronouncing her name "Mike" and gets surprised when she asks him to meet her.
- Kissing Cousins: Scott has a nightmare in which Mieke is so desperate to cut Scott out of her life that she has sex with her own cousin.
- Ms. Fanservice: Once it's revealed that Mieke is an attractive girl, her hotness is emphasized as much as humanly possible. Most of these are in Scott's imagination, but it gets to ridiculous levels when the two finally meet in person and immediately shag each other's brains out in a confession booth.
- Satellite Love Interest: She gets practically next to no character dynamic with any other (major/supporting) character other than Scott, and even with Scott it was barely a few short interaction scenes.
