Ranking The Best Sketches Of 'I Think You Should Leave's Second Season | Opinions | LIVING LIFE FEARLESS

Ranking The Best Sketches Of ‘I Think You Should Leave’s Second Season

I Think You Should Leave with Tim Robinson is never on Netflix’s Top 10 lists. It doesn’t show up in the streaming ratings put out by Nielsen or any of the other outfits that release streaming audience memberships. 

But among a certain cohort — on Twitter, in comedy spaces, otherwise among the “extremely online” — the sketch show is massive. It’s quoted, referenced, and memed constantly.

 It’s very clearly going to be a comedy touchstone for a generation of rising comedy writers and comedians. When actor Bob Odenkirk suffered a health crisis this week, fans of his shared and quoted his recent I Think You Should Leave appearance amid their good wishes. 

The series’ Second Season arrived in early July, and it was very clear early on that the new season was just as strong as the first. The structure of the series — just six episodes, about 15 minutes each — is especially conducive to watching the entire season in one sitting, and multiple times. 

After 5 or 6 watches of Season 2, here’s my ranking of the ten best ITYSL sketches of Season 2: 

 The Capital Room 

This parody of Shark Tank is quickly taken over by Patti Harrison’s host, who quickly reveals that she made her money, not from cutthroat business expertise, but rather because she sued the city after she was accidentally sowed into the Charlie Brown balloon’s pants at the Thanksgiving day parade. This has led her to develop an unhealthy wine habit. 

This wouldn’t work if not for Harrison’s crazy energy, but that energy is really something to behold. 

Calico Cut Pants

The longest sketch of the season is an elaborate office two-hander with Tim Robinson and his fellow ex-SNLer Mike O’Brien, in which Robinson pitches a website called Calico Cut Pants, which comes preloaded with urine stains. BUT, the pants aren’t real, and it’s an elaborate ruse to get people to donate to the website in order to keep it going. 

Sloppy Steaks 

This one goes from the common problem of an adult thinking his friends’ baby doesn’t like him, to an even weirder place — Robinson’s Shane thinks the baby is judging him because “I used to be a huge piece of shit.” And was a specific type of dude who enjoyed a delicacy known as “sloppy steaks” — pouring glasses of water on top of steaks. 

Professor Houses Dylan’s Burger 

I Think You Should Leave has a record of finding obscure, fantastic older actors, going back to Ruben Rabasa, from the car focus group bit in the first season. This time it’s veteran character actor Bob McDuff Wilson, who plays a professor out with some of his old students, in which he outs himself as a glutton — eating one of the students’ entire burger — and also something of a pervert. 

Insider Trading Trial

Another fantastic long sketch, which begins with a corporate malfeasance trial, which soon segues entirely of a witness reading aloud incriminating text messages of the defendants making fun of a silly hat belonging to Brian (Robinson), their coworker. It just escalates and escalates, until “I swear to fucking god he tried to roll the hat down his arm like Fred Astaire.”

Ghost Tour 

Another I Think You Should Leave Sketch about someone in a normal situation acting very not-normal. This one is a ghost tour of an old house, which is established as the “adult” tour, so one participant (Robinson again) decides to constantly make sophomoric dirty statements. Robinson’s delivery of “do any of these… fuckers…” is especially memorable. 


Another classic, in which the teacher in a drivers ed class (Robinson) shows an older instructional video featuring a driver (Harrison), whose job involves tables, and is angry that the tables keep getting dirty; this presumably leads to an awful accident. And for some reason, Robinson won’t tell the students what the woman’s job is, or what the tables are for. 

Once again, Harrison sells it with the delivery. 

Dan Flashes 

An outstanding two-parter, the first half of which is an office argument, in which it’s made clear that an executive (Robinson) isn’t eating because he’s spending his per-diems on shirts at a store called Dan Flashes. The second part is a commercial for the store, featuring men fighting over the pattern-filled shirts. 

It seems to be a male parody of those old Barney’s sales in New York, where women would fight over clothes, although I guess it’s funnier when nerdy men do it. 

Detective Crashmore 

The Season’s other great two-parter is the saga of Detective Crashmore. The first part is the trailer for a wildly violent cop thriller, about an old bearded detective who just kills everyone and curses throughout, until the reveal that the cop is being played by Santa Claus. Part 2 is a press junket for the movie, in which Santa gets angry at all the Santa questions, and then recites such movie-junket bullshit as “cosmic gumbo” and “it moves at the speed of jazz.” 

The writing is great, but what sells it is the actor playing Santa, who goes by the wonderful name of Biff Wiff. 

Coffin Flop 

This starts as a commercial parody, in which Robinson calls for his TV network, Corncob TV, to remain on Spectrum cable. But then he shares some footage from the network’s signature show: Coffin Flop. Which is exactly what it sounds like. 

The first time I saw Coffin Flop is the hardest I’ve laughed at anything in at least five years, and it hasn’t gotten less funny on repeat viewings. 

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