I Think You Should Leave Season 2: Ranking Every Sketch

From Dan Flashes shirts to some very sloppy steaks, I Think You Should Leave season 2 delivers another round of superb sketches.

Tim Robinson as Karl Havoc in I Think You Should Leave season 2
Photo: Netflix

How on Earth did we survive two years without new episodes of Netflix’s brilliant sketch comedy series I Think You Should Leave with Tim Robinson? The first batch of six episodes premiered on April 23 of 2019 and proved instantly iconic. 

Contained within the season’s roughly two-dozen sketches was absolutely hilarious and essential comedy that provided ample memetic kindling for the internet’s conversational fire. For the focused enough mind, it’s entirely possible to communicate with one’s friends exclusively in I Think You Should Leave memes. Lord knows, I’ve tried it.

Thankfully, ITYSL season 2 has finally arrived on Netflix after its COVID-19 delay. It features 28 sketches that range from “pretty funny” to “I can’t stop laughing. Oh God, I can’t stop laughing. It hurts, surely this is the end. Surely, I will die.”

Check out our rankings below and then begin yelling at our chances like Spectrum is dropping your network.

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28. Credit Card Roulette

If nothing else, Tim Robinson and I Think You Should Leave co-creator Zach Kanin are incredible comedy scouts. Through two seasons, the show’s sketches have been a who’s who of up-and-coming comedic talent, like the wonderful John Early who is featured in this sketch. Unfortunately Early is not served well by the material here, which doesn’t rise to the same ludicrous heights as season 2’s other sketches. The best moment is Early’s immediate resolve that he’s not paying the bill, but the sketch doesn’t go too far after that. 

27. Dave’s Poop Double

The sketch that serves as the cold open of season 2’s final episode doesn’t get things off to the best start. The concept of Tim’s “Luka” hiring a guy who looks just like his coworker Dave to take monster shits every time he gets up is certainly fun but missing an important layer of added absurdity. Luka is probably the best name for any of Robinson’s random characters yet though.

26. Little Buff Boys Pt. 2

Season 2 features many more callbacks to previous sketches than the first season did. This followup to Little Buff Boys is the worst of the bunch but still quite funny. Perhaps the only thing more absurd than a Little Buff Boys competition is someone being proud of running “one of” the biggest LBB competitions in the Greater Cincinnati area. This sketch also passes up an easy Cincinnati Chili joke in favor of creating the truly vile “cherry chuck salad.”

25. Detective Crashmore Trailer

This trailer for action thriller Detective Crashmore is funny enough on its own but doesn’t reach another comedic level until the AOL Blast interview two sketches later. Still, I unironically want to see an action film with a lead character whose main quip is “Eat fucking bullets, you fuckers. You fucking suck. You fucking SUCK!”

24. I Should Have Got That

I Think You Should Leave deserves a big spread in AARP magazine. No other sketch show revels in the talents of older comedians quite like this one. After 81-year-old comedian Ruben Rabasa stole the show in season 1, season 2 ups the ante with many more sketches letting old folks shine. It’s Bob McDuff Wilson’s turn this time around and his child-like obsession with his student’s burger kills right up until the shockingly dark kicker.

23. Office Surfing

“I almost killed myself, Jullliieeeeee” is one of the best line-reads of the season. The sketch it’s built around isn’t too remarkable but man, does Robinson knock that one out of the park. 

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22. “No, I Don’t Know How to Drive”

This is a quickie but a goodie. Robinson’s characters break down in tears quite often this season and this is one of the better occasions. How far have Tim’s characters come – from reveling in the existence of four-wheeled motorcycles to looking at the inside of a car and weeping “I don’t know what any of this shit is and I’m fucking scared.”

21. The Capital Room

Speaking of top tier comedic talent, thank God Patti Harrison stopped by another season of I Think You Should Leave. This time around, we get two heaping doses of Patti. This one, the first of the two, is the inferior but still quite great. In the span of roughly 30 seconds, Harrison unveils the saga of a woman who A. Got sewn into the pants of the Thanksgiving Day parade Charlie Brown float, B. Hates all bald boys, C. Sued the city and won a fortune, D. Is now helplessly addicted to wine, and E. Is tragically self-aware that her money will run out soon.

20. But It’s Lunch

Just like last year’s opening sketch, “But It’s Lunch” (this is probably a good time to mention, that I’m naming all of these things myself. You could very easily call this the Hotdog sketch but that would confuse it with last year’s hotdog sketch) sets the perfect opening mood. The sight gag of Robinson’s Pat trying to stealthily eat a hotdog is wonderful, and the fact that things so quickly escalate to hotdog surgery and puke is just sublime. 

19. Carber Hotdog Vacuum

The follow-up to “But It’s Lunch” occurs a full two episodes later and proves to be a hell of a pay-off. Robinson’s unnamed character (who is obviously Pat) very quickly reveals that there is one very specific reason he made this hotdog vacuum invention and you’ll never guess what it was. We all make mistakes. We shouldn’t be fired for them.

18. Insider Trading Trial (Stupid Hat)

This sketch somewhat mimics the experience of trying to explain what I Think You Should Leave is like to someone who has never seen it. “So, this guy took too small a slice of toilet paper…” or “…and then he has to have to have sex with his mother-in-law.” “Insider Trading” rotely describes the bizarre behaviors of one of Robinson’s deeply strange characters, Brian, as it’s being read into the court record. Brian and his stupid fedora with the safari flaps is in attendance to provide a visual aid. As are some hilarious flashbacks in which Brian attempts to roll the hat down his arm like Fred Astaire and instead encounters only wheelchair grease. 

17. The Ice Cream Store is Closed Today

Before he was a criminal lawyer, Bob Odenkirk was one of the most legendary sketch writers of all time. It’s only fitting that he stop by ITYSL season 2 to provide his comedic blessing. Odenkirk is great from the get-go but this one doesn’t really get rolling until the end when Robinson finds himself truly immersed in the fictional life of this sad old man. “His wife’s sick but she’s gonna get better” is a shockingly emotional moment amid pure farce.

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16. Barbie and the Blues Brothers

This is the sketch that climbed the most in my rankings upon a second viewing. What first seemed to be a waste of Conner O’Malley’s manic comedic energy became a semi-classic once I submitted to its strange vibes. I don’t even know what to call this one but Robinson’s character refusing to stop dancing as Barbie the dog melts down is hilarious. O’Malley is better served by last season’s “honk if you’re horny” sketch, still he gets some bangers in this time around like “She thinks he’s a whole new guy because of the glasses and the hat” and “it’s her house, she’s doing what’s right!” Robinson once again closes this nonsense out with some well-earned tears. “It’s just me, Barbie. I’m not the Blues Brothers.”

15. Jaime Taco (I Love My Wife)

“Jamie Taco” is a prime example of just how rapidly (and how well) I Think You Should Leave is able to veer into pure nonsensical genius. At the top, this sketch comes perilously close to making an actual statement about how men are too quick to pretend like their wives are horrible nags. This sketch, however, has its sights set on something much dumber…and therefore better. Our hero (played hilariously by Richard Jewell’s Paul Walter Hauser) loves his wife because she helped him through his darkest moment, which just so happens to be when snotty young actor Jamie Taco refused to let him say his Henchman lines in a play.

14. Comos Restaurant 

All hail the return of the great Tim Heidecker! Heidecker, of Tim and Eric Awesome Show, Great Job! fame, is one of the few comedians with a strange enough sensibility to be reasonably seen as an I Think You Should Leave forerunner. His season 1 turn as a walnut-obsessed jazz douche is a classic and this one reaches similar heights. This time, Heidecker’s character, Gary, and his lovely date, Janeane (Tracey Birdsall), have good reason to be annoyed by their date night at the sci-fi cosmos restaurant being interrupted by some hacky jokes. Of course, they use this opportunity to reveal that Jeannine’s mom used to drink puke for the Davy and Rascal radio show to pay for school supplies. It’s oddly refreshing to have a Heidecker character given a game partner and Gary and Janeane make one great team.

13. Detective Crashmore Interivew

While the Detective Crashmore trailer is the setup, this interview with AOL Blast is the punchline. Detective Crashmore is played by Santa Claus, because why not? Actor Biff Wiff’s gruff, nasally Midwestern timber is the perfect accent to accompany this lunacy. This is a Santa who in one breath demands to be taken seriously as an actor (Billy Bob Thornton-style) and in the next admits to seeing everyone in the world’s dick.

12. Sloppy Steaks (I Used to Be a Piece of Shit)

From here on out, it’s nothing but absolute homeruns. “Sloppy Steaks” could very well have been number one on this list and few would have batted an eye. The setup here is amazing as it gives Tim Robinson a reason to essentially have beef with a baby. The baby cries because he knows Robinson used to be a piece of shit. But don’t babies understand that people can change? That’s funny enough to begin with, but the real gut-busting moment here is the reveal of what “being a piece of shit” really means. In this case it means slicking one’s hair back and dousing the steaks at Truffoni’s with water to make sloppy steaks.

11. Johnny Carson Impersonator

Just a quick rundown for those who are confused…

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Johnny Carson = Can Hit.
George Kennedy = Can’t Hit.
George Bush = Can’t Hit. 

10. Driving School (Her Job is Tables)

This is the rare I Think You Should Leave sketch that actually provides an answer to all the lunacy. As Robinson’s character’s Driver’s Ed class watches Patti Harrison’s actress in some dated videos, they can’t help but wonder what she does for a living. “Tables,” Robinson answers over and over again. This would be funny enough on its own but the reveal that Harrison provides tables to Monster Cons is a rare and valuable moment of “Ohhhhh that’s why” for this show. Equally as valuable is Harrison, who really sells that those tables are her lifeblood.

9. Claire’s Ear-Piercings

One has to wonder how much time goes into choosing the perfect “order” for the sketches in I Think You Should Leave. Two seasons in a row now, the show has selected pitch perfect opening and closing sketches. This closing number is oddly melancholic as the Claire’s orientation video for girls who want to get their ears pierced somehow gives way to one 58-year-old man named Ron Tussbler’s existential dread. If we really get to see the “highlights” after we die, forcibly fake laughing every ten minutes to make the voyeuristic experience all the richer sounds like a good strategy and not sad at all. Hang in there, Ron.

8. Little Buff Boys Competition

What. A. Crop. It was a virtual certainty that ITYSL season 2 would feature a spiritual successor to the classic “Baby of the Year” sketch in season 1. Thank God “Little Buff Boys” is up to the challenge of replicating that magic. This one has all the right elements to be another hit: Sam Richardson (in a wig this time, no less), a grand pageant hall, and some precocious youths. Troll Boy also joins the canon of young ITYSL characters who everybody instinctively hates alongside Bart Harley Jarvis.

7. Tammy Craps

There’s something weirdly nefarious about this commercial for a poisonous doll that doesn’t have farts in her head anymore. It’s a criticism of late stage capitalism crossed with the cursed nature of the Annabelle movies…while not being like either of those things at all. In reality, this is just another absurdist concept sprung from the terrifying inner depths of the writing staff’s mind. It also happens to be a particularly great one. The girl weighing her clothes down with rocks so she can hit the magical 60-pound threshold to safely play with Tammy Craps is one of the best gags of the season.

6. Karl Havoc

“Little Buff Boys Competition” and another upcoming sketch are likely to produce the lion’s share of memes and quotes from this season of ITYSL. But the one quote that’s stuck in my mind most aggressively comes from this hilarious episode 1 clip. The sight of Robinson’s Carmine Laguzio posing as the dead-faced freakshow Karl Havoc and muttering “I don’t want to be around anymore” is quite simply one of the funniest things I’ve ever witnessed. This is a marvelous, unnerving, utterly hilarious sketch. That there are somehow five better sketches speaks to how strong this season is. 

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5. Dan Flashes Pt. 1 (Office)

I Think You Should Leave is now two for two in introducing the most cutting edge items in men’s fashion. Season 1 featured the arrival of the highly practical TC Tugger shirt. Now season 2 ups the ante with the stylish Dan Flashes. This sketch succeeds because it takes a simple question “Why is Mike laying down during a business meeting?” and divines the most outlandish answer possible. Mike isn’t eating because he’s spending all his money on Dan Flashes shirts. 

4. Dan Flashes Pt. 2 (Hotel Menu)

It’s one thing to introduce a hilarious concept, it’s another thing entirely to put it into practice. This second entry into the Dan Flashes canon is amazing. Back in part 1, it seemed as though the intricate patterns on the Dan Flashes shirts have a hypnotic effect on men who look exactly like Tim Robinson. Seeing the reality of that – pasty men battling one another to get their credit cards to the cashier before the other – is truly hilarious stuff.

3. Coffin Flop

This is the second sketch of the entire season…the second! And holy shit, does it set a strong precedent for what’s to come. This impassioned message from the Corncob TV CEO for Spectrum to save his network and its precisely one television program is a masterclass in shock humor. Watching body after body busting out of shit wood somehow never loses its grim luster. Somehow, in a sketch that features dozens of naked corpses flopping to the ground unexpectedly, it’s Robinson’s monologue that hits the hardest. “This world is so fucked up. And people are mad at me because I showed a bunch of naked dead bodies with their spread blue butts flying out of boxes? Really?”

2. Calico Cut Pants

Every episode of I Think You Should Leave season 2 features five sketches save for episode 4 which has only three. And that’s because episode 4 is dominated by a near 10-minute epic called “Calico Cut Pants.” In many ways, Calico Cut Pants is the platonic ideal of an ITYSL sketch. It takes place in a nightmarish world where every bizarre action only leads to an even more bizarre reaction. Nothing ever cools down. There is always something stranger on the horizon.

In this instance, Mike O’Brien (longtime SNL writer and the creator of the terminally underrated comedy A.P. Bio) plays an office drone who enters into a living hell merely because his co-worker helps him out of a mildly annoying social jam. Robinson’s character introduces him to a website that advertises pants with piss stains on them. That’s all well and good but once you know about Calicocutpants.com you Always. Have. To. Give. It’s like PBS, but more demonic. This remarkable sketch includes everything that’s great about this show, right down to characters with inexplicable idiosyncrasies like Tim Robinson’s adamance that doors must always be held open for him.

1. Ghost Tour

The funniest moment in ITYSL season 2 (and maybe the funniest moment in the history of the world) occurs in this sketch. Tim Robinson’s character has been admonished for his potty mouth during a ghost tour over and over again. The tour guide even said he’s ruining his job. But this poor man sincerely cannot understand why he’s in trouble. This is a tour for adults and he’s following the rules by using adult language. Like any good Robinson character, he truly believes that he’s the sane one and it’s the rest of the world that’s taking crazy pills.

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So in his darkest moment, the man musters up his strength through tears and delivers the following query:

“Not trying to be funny. Not trying to get a laugh. I don’t want anybody to have the worst day at their job. But. Do any of these….fuckers….ever blast out of the wall and have, like a huge cum shot?”

Cue: riotous, damn near apocalyptic laughter. What a treasure and blessing this whole show is.

I Think You Should Leave season 2 is available to stream on Netflix now.