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  • Most of the hilarious moments are in the "Favorite Fan Moments" videos.
  • Some of the hijinks that Stephen and his roomies get into while in the early days. Notable mentions:
    • Alex being distracted by a discussion with the others, forgetting he was baking bread.
    • Stephen brings up the color of the carpet. He says it's blue, Alex insists it's green, and even takes a photo and ups the saturation in an image editing programme to prove it. They ask Dan to give a deciding opinion, only for him to Take a Third Option and say it's black. Eventually it all leads to this:
    Alex: Okay, you've been filming the "Carpet Debate" for about 25 minutes now!
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    • Stephen ended up with Dan's messenger login on his laptop, so exploited it to send a message to Alex every day for weeks which all took the format "I AM DAN" "(link to Taco Bell Wikipedia page)" "(random vaguely related comment)". He eventually revealed the prank to both of them and it became a very popular video, producing memetic lines such as "1962 Was A Long Time Ago".
  • Several of the vlog titles, such as "Carpet Debate" and "Sex Into Children's Eyes".
  • Emile constantly messing up the ending.
    Stephen: Thank you so much for watching, and as always, let's meet back tomorrow...
    Emile: ...6 5 4 3 2 1?
    Stephen: Oh, Jesus Christ.
    • Day 2161 featuring Masae and the Runaway Guys ends with Emile nowhere around. So Stephen has Masae end the blog and jokes that he will put an image of Emile appearing. Then an image of Emile does show up.
    Emile Image: What did you say?
  • On Day 2002, Stephen and Mal get a pet door, and the results of them trying to get the cats to use it were pretty funny.
    Stephen (after watching Sagan walk away): We're doomed...
  • Day 1697, when Stephen and Mal go to visit Dan and decide to play Coup. Dan tries to assassinate Stephen. Stephen claims to be Contessa, which blocks assassination. Dan considers challenging him, but decides not to.
    Stephen: But Dan, guess who's Contessa?
    Dan: Not you...
    Stephen: Right. So, you're not challenging me?
    Dan: Okay, well now, if you say anything else besides Contessa...
    Stephen: So he doesn't challenge me. Is it my turn? Okay. I'm the Duke.
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    • And later on...
      Dan: I'm the Captain, and I'm stealing your sh—stuff.note 
      Stephen: Okay. (he laughs)
      Dan: Are you sure?
      Stephen: Mm-hmm.
      Mal: Okay, Stephen, your turn.
      Stephen: I'm the Duke.note 
      (Stephen and Dan start laughing)
      Dan: Just to let you know...
      Stephen: I'm the Duke! ...Your turn.
      Dan: I'm the Captain.
      Stephen: I'm... the Duke!
      (Stephen and Dan are gradually losing it)
      Dan: I'm the Captain! (he cracks up) You know what's happening here, right?note 
      Stephen: I'M the Captain!
      Dan: No you're not! You are not the Captain. (pause) YOU ARE NOT THE CAPTAIN!
      Stephen: You don't know that!
      Dan: Shut your mouth, just show me that you...
      Stephen: (card shows Contessa) I'm the D—I'm the—oh. I thought I was the Duke!
  • Day 1984 involves Stephen showing his parents the Smash Brothers characters. They see Ness and don't know it.
    Stephen: Who's that?
    (Beat)
    Stephen: Oh lord...
    Debra: Lucas.
    Stephen: Oh my god... (Mal laughs in background).
    Steve: Pointer?
    Stephen: Oh please, oh please don't-
    Debra: Ninten!
    Stephen: Please... what?! You guessed Lucas and Ninten?! Are you kidding me?
    Debra: Who are they?
    Steve: Pointer.
    Stephen: Oh my god, please, please tell me you know who this is. Please.
    Debra: It's you.
    Stephen: (laughs) You don't know his name? You really don't after all these years? You don't know his name... he has a four letter name.
    Steve: Sour.
    Stephen: His name is Ness.
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    • When he shows them Dixie Kong, the guesses get even more ridiculous.
      Debra: Diddy?
      Stephen: No...
      Debra: Diddles.
      Stephen: Diddles? DIDDLES Kong??
      Steve: Diddly! Diddly Kong!
      (Stephen cracks up)
  • The announcer's voice in Mario Kart Arcade GP DX when Stephen, Chugga and Masae play it on Day 1992...
    Chugga (imitating the announcer): KART NUMBAH ONE! KART NUMBAH TWO! KART NUMBAH ONE! KART NUMBAH TWO!
  • Behold: Day 2069, "Steve Guessed 'Abortion Clinic'". Stephen, Mal, Steve, Debra, Kyle and Karley play a game of "Telestrations", which is like a combination of "Telephone" and "Pictionary". The highlight begins with Debra's drawing of an "animated movie". Mal guesses "Kindergarten", and hands it off to Stephen. Stephen draws a picture of a Kindergarten class and hands it off to Steve. Steve guesses "abortion clinic", hence the title of the vlog. Kyle is now tasked with drawing a picture of an abortion clinic, and Karley guesses "liposuction place".
  • This exchange at the end of Day 2163:
    Emile: "Well, I'm the mouth, Tim is the butt, Stephen's the legs and Jon's the Canadian.
    (Beat)
    Jon: Everyone's favorite body-part.
    Stephen: The Canadian? Now is that a sex organ?
    *Emile starts giggling*
    Jon: No, it's your Vernacular, get it right!
    Stephen: *sighs* I'm gonna have to censor all of this. *Jon laughs* You can't say the V-Word, gracious sakes. Cheeze and Crackers, Jon. *sighs again*
    Jon (off-screen) : Manners! *Stephen laughs*
    Emile (off-screen) : Vernacular blood is so gross.
    *Stephen's smile fades into looking vaguely disturbed*
    Subtitles : (Stephen is filled with despair)
  • The entire recap of Stephen, Masae, and The Runaway Guys' trip to Steak 'n Shake.
    • Stephen asks the guys to summarize their experiences in two words. Emile: "You suck."
    • Jon: "Mayo" and "mustard".
      Jon: I ordered a hot dog with no mustard. I instead get a hot dog with a lot of mustard. And some mayo.
      Stephen: It was so much fun watching you eat that; you have no idea.
      Jon: I got two bites in, and got hit by so much mustard that I could not taste anything for the rest of the hot dog. I'm not even convinced I ate food.
    • Masae: "Nugget munch."
      Masae: (showing a chicken nugget that looks half-eaten) I did not take that bite. Just sayin'. It came to me like that.
    • Tim: "Burger butt."
  • The way Alex proposes to Hayley. It's hilariously nonchalant; he gets on one knee, takes out the ring, and just remarks "Look it's this thing. Will you marry me?" After shocked laughter and hugging, she simply replies "Sure." They truly were made for each other.
  • Stephen managed to do a major, multi-day screwup... by plugging his microphone into his camera's headphone jack.
  • A viewer (or more likely more than one) seized on Stephen doing a creepy voiceover for a plush dog with a heart in its mouth to create the character of "Mr Dyslexic Heart Bear", who occasionally sends Stephen rambling Cut-and-Paste Note letters. Yes he does. Yes he does. After some years without a mention, another one appears in a 2016 edition of Stephen Mail in which he claims to have mailed his father to Stephen and Mal. This turns out to be a much larger similar plush dog.
    Stephen (as Mr Dyslexic Heart Bear's Father): "Don't talk to me or my son ever again!"
  • Stephen had another surgery. Some of his loopy, post-surgery ramblings are funny. For example, when he's getting ready to eat his chicken broth:
    Stephen: Like, that's my only meal... anymore, right? Like, I couldn't have Chick-Fil-A?
    Mal: Just the rest of your life, chicken broth.
    Stephen: Oh, you're full of it! (sip)

    Stephen: I don’t know how my surgery went, I wasn’t there.
  • A COPY OF DEAL OR NO DEAL FOR THE NINTENDO DS.
  • Two great moments from Vlogmail August 2018:
    • Stephen and Mal are sent Friends Trivia and Stephen explains he has never watched it so he would fail very quickly. For no reason, he then becomes obsessed with asking Mal if he is right about identifying Joey (looking at the group on the box art), and comes up with his own names for all the other characters.
    Stephen: Joey! Is that Joey? That's Joey! (much later) One of 'em's Anita.
    Mal: ...No!
    Stephen (points to characters in turn): Joey...Anita...Jennifer Aniston...Clyde? CLARK!
    Mal: No!
    Stephen: Shut up, it's Clark! Um...Tinus? Tinus isn't a name. I just said a word. And Jane.
    • They are sent a copy of Boom Blox with packaging still on, and Stephen excitedly sings (in a Wayne's World type manner) what he thinks is a tagline on a fake warning sticker that's part of the game box art, but turns out to be an actual warning sticker on the outside:
    Stephen: Boom Blox! Boom Blox! The Steven Spielberg E-A Game! War-ning! Keep away from small children, the thin film may cling to - oh, it's not part of the game... (corpses)
    Mal: It's part of the plastic.
    Stephen: I thought it was part of the advertising on the game! I was like (does 90s radical hand gesture) "WARNING! Keep away from small children! Boom Blox! The...thin film may cling to their nose and mouth, and prevent breathing..." and I was like "Oh, that got dark." (Mal laughs) "Mr Spielberg, I enjoyed the game, but the part about the children, um, choking to death, that was a little dark. Maybe leave that part out of the sequel."
  • The Bean Boozled Challenge with Chugga and Masae. Everyone's reactions to getting a terrible jelly bean flavor are as priceless as you'd expect. At the end, Masae offers Chugga ten bucks if he could down as many beans as he can all at once. The result? Each disgusting flavor smacking the poor guy's taste buds one by one.
  • An otherwise normal Breakfast Stream goes off the rails due to two incidents:
    • Stephen jokes that an alert looks like someone who has cut off their fingers, IMMEDIATELY before reading out a donation (submitted earlier) from a fan who had just cut off their fingertip in a work accident - he immediately felt guilty about it.
    • Stephen talks about how his mom has the sacred hospitality attitude that when throwing a party, there should be enough food for any circumstance - and makes up the character of "Potato Boy, who only eats potatoes", saying he should be able to do that and there should still be potatoes for everyone else as well. The chat responds by gifting subs to an actual Twitch user named PotatoBoy, which is slightly funny...and then they keep on finding more Twitch users with Potato Boy-related names to gift subs to as an Escalating Punchline. Stephen slowly descends into madness as he considers the Fridge Logic of there being so many people who wanted that username that there's a PotatoBoi, a PotatoBoy15, a PotatoBoy99, etc. ...Stephen then jokes that PotatoBoy's mom is called 'SpudMom', only for the chat to find a Twitch user named 'spudmom7' to gift a subscription to. By the time the stream is ending, subs have even been gifted to a PotatoStephen, a PotatoMallory and a Potato_Dan (who Stephen, on the edge of sanity, notes has left room for a PotatoDan minus underscore).
  • In the last Breakfast Stream before The Runaway Guys' Colosseum 2019, JoshJepson guests and somehow Stephen ends up suggesting that his rapper name would be "Li'l Li'l Jep Jep". After Josh later mistakenly says 'the letter five' rather than 'the number', the chat suggests that this is the name of his first hit single ft. Peggy.
  • Stephen's "Behind-the-Scenes" vlogs, filmed during The Runaway Guys Colosseum 2019, showcase a lot of the hilarity that ensued behind the camera.
    • While filming FamilyJules' bit for the sitcom intro, which was merely a shot of him stepping out of the shower and spraying his hair, Jules accidentally hairsprays himself in the eyes. Hilariously enough, they ended up using this take in the actual intro.
    • ProtonJon attended a pre-release event for Borderlands 3 prior to Colosseum, so by the time Stephen picked him up from the airport, he had a bunch of exclusive swag on him straight from the event. One of the items is a plastic mask that he puts on just for the hell of it; Stephen is quick to point out how incredibly suspicious they're gonna look during the drive back.
      Stephen: Yeah, we won't get stopped. You ain't makin' it to Colosseum, or any of us!
    • As it turns out, the screams used in the "Balls Are Alive" bumper were provided by the other guests at the stream. When Stephen records some individual screams from Masae, she gets so into it that she decides to chase him around the kitchen while screaming like a banshee.
    • In the uncut version of the "Honor" bumper (where Jon hits Tom Fawkes over the head with a cardboard tube, but gets cut off with a "We'll Be Right Back!" card before the impact), we actually do get to see Tom get hit, and Jon even whacks him again for good measure.
    • While filming Masae's bit for the sitcom intro (where she pulls Emile out from under the pool table), she accidentally trips and falls to the ground.
      Tom: Alright, use that one!
    • While filming the intro's Group Picture Ending, Stephen tells Tyler to leave some room for Jon... using some very poor word choices.
      Stephen: Spread your legs for Jon.
      Josh and Marriland: Whoa!
      Tom (singing uncomfortably): So no one told you life was gonna be this way... *clap clap clap clap!*
    • Stephen and Tom film a (cut) bumper where LORD DONA'TOR runs on the beach; the problem is, it's so windy that his hood keeps flying off of his face, so he eventually resorts to holding the hood down with his teeth.
    • Stephen ends one of the vlogs by zooming in on Josh, who tugs at his shirt to show off the VSX logo his chest. Stephen comments, "Oh I thought you were grabbing your...nipples."
    • Tyler's entire nonsensical rant about sleep.
      Tyler: I think the sun is honestly just a giant facade. I think it was all made up by the government to control us-
      Josh: Tyler Tyler Tyler Tyler... people are trying to sleep, it's 5 AM.
    • On the final night of Colosseum, the gang heads over to Waffle House for a celebratory dinner. Keep in mind, the diner has a jukebox containing an entire album of Waffle House themed-songs, including Stephen's favorite hit, "Raisins in My Toast". So guess what song he decides to overplay that night?
      Stephen: Josh, you don't understand... Josh, I get four songs.
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