Top 10: I Think You Should Leave with Tim Robinson Sketches (Season 1)

I Think You Should Leave with Tim Robinson is a sketch comedy show co-created by Zach Kanin and Tim Robinson (who also wrote and produced the show). For whatever reason I missed this show when it first came out back in April 23rd 2019, in fact I was actually recommended it by the Game Grumps who quoted some of the sketches during a playthrough on their Let’s Play channel.

Anyway, since I had some free time to fill during 2020 and because I love sketch comedy I decided to check it out and I do not regret it. Plus with season 2 scheduled for release today on July 6th 2021, it seemed like the perfect timing to do a Top 10 for season 1. 

1. The Day That Robert Palins Murdered Me
So this sketch is from the fifth episode of the show, and it is just a masterclass in surreal comedy, one which easily claims the top spot on this list. I have watched it a few times since the first time I saw it, and it’s made me laugh consistently every single time. We have Rhys Coiro, with his rich baritone vocals, clearly meant to evoke in both style and delivery the legend, Johnny Cash giving a recording studio executive ‘something new’ and starting off a phenomenal, country tinged epic. Meanwhile, oblivious to all that Tim Robinson’s character, the bassist, begins to freestyle some elaborate farce about spooky skeleton people who use bones and worms as money and who pull your hair. They duel for the storytelling throughout the song, with Coiro’s character clearly becoming agitated but nonetheless still just going along with it. This sketch was just so funny, a particular highlight being Robinson’s character’s trademark incredulity. 

2. Babysitter
A consistent trend of I Think You Should Leave are characters played by Robinson who cannot stop digging themselves into holes. In this sketch, also from episode five, he is prompted by his partner to tell a simple white lie about why they were late to a party, specifically that the babysitter was late meaning they were late. He unfortunately elaborates a little too much, and outright makes up a story about a hit and run and how the cops aren’t too interested because the victims weren’t real people. It’s dark and a little offbeat, but with the escalation, and Robinson’s lack of any real self awareness it’s just hilarious. Robinson’s character is questioned by a concerned friend about the incident and because he doesn’t want to admit he was lying Robinsons character threatened to embarrass his friend. I think it’s a sketch which would have struggled without Robinson’s talents but honestly it’s genius and came very close to taking the top slot itself. 

3. Chunky
This sketch is from episode 6 and it’s one of the rare sketches where Tim Robinson isn’t the weird one. It has him hosting a game show, which has yet to properly define itself, specifically the show’s mascot ‘Chunky’ who reminds me of the ‘Whammy’ from Press Your Luck who doesn’t quite know what his deal is yet. It stars the phenomenal talent of Andy Samberg (noted for co-founding and being a member of The Lonely Island, being an SNL cast member from 2005 until 2012 and for playing Jake Peralta on the Fox, and later NBC, police sitcom Brooklyn Nine-Nine) as one of two contestants on the show, who bears the brunt of Chunky’s experimenting. He plays expertly off of the chaotic and ill-defined energy of Chunky. Some particular highlights include Robinson’s reactions to Samberg’s character swearing and to Chunky talking.

4. Bozo
Another sketch from episode 6, and one which elevates a simple human interaction, something most anyone would be familiar with, and turned it into something truly magical. I mean all he would have had to do is say that he wasn’t familiar with the viral videos he was being shown but instead as I referred to up top, he just digs himself deeper. Forget for a second the actual dubbing over, which was hilarious and also very quotable. But just Robinson’s ridiculous overcorrecting and defensiveness, it really makes the whole sketch. 

5. Nachos
A sketch from episode four, and one which kind of exemplifies the fact that Tim Robinson’s characters tend to tell a lie to avoid awkwardness and rather than come clean just keep piling more lies on top. I think what I liked most about this one was just how amazingly uncomfortable it all was. His vehement refusal to back down, continuing to spin more easily disprovable lies and responding with an increasingly incredulous ‘WHAT’. It’s just so funny. 

6. Traffic
I remember someone saying that comedy usually derives itself from a sane person in a crazy world or a crazy person in a sane world, and this sketch, from episode four, kind of exemplifies this idea. In it we have someone displaying an extreme overreaction to a ‘honk if you’re horny’ bumper sticker. He makes Tim Robinson’s character’s life hell, following him around and aggressively honking his horn. He even interrupts the funeral of Tim’s mother in his quest to satisfy his overwhelming horniness. Conner O’Malley’s physical acting throughout this sketch, in particular his pained expression, really make this sketch stand out. I think the highlight though was that despite the bizarreness of the situation and the distress this man has caused, especially while dealing with his mother’s death the sketch manages to end on a surprisingly uplifting note, with Robinson singing a pop ballad as a tribute to his mom. 

7. Brooks Brothers
I think this sketch, from episode 5, was the first one I saw from the show and it’s wonderful in its absurdity. Much like ‘Both Ways’ it encapsulates Tim Robinsons comedy style, and sees him caught in another obvious and yet elaborate lie. It takes a violent left turn from a guy dressed in a hot dog costume crashing into a clothing store, to him going off on a personal diatribe about how people are so addicted to their phones that people don’t talk to each other anymore, which would have been a fine and valid point but he also managed to drop the names of several very specific porn sites in the process. It’s just so funny, a particular highlight was the character of Donald, who was dressed in a suit, which made him look as much like a hot dog as possible without actually wearing a hot dog costume like Tim Robinsons character was. His sad little ‘Oh No’ just really got me. 

8. Party House
This sketch from episode 6 is just great, it manages to overlay something as serious as an intervention with an extremely distracting location like the house of Jim Davis, the creator of Garfield. It is filled with merch from the popular comic strip featuring the Monday hating, Lasagne loving, orange cat. It’s incredibly absurd to have someone listen to his best friend talk about how his drinking is destroying their friendship while he is sitting on a reclining sofa designed to look like Odie the good natured dog, also from the Garfield comic strip. I think though, had this just been left up the the props and the overall premise it might not have been strong, but the really power behind this sketch comes from Kate Berlant’s character, credited on IMDB as ‘Owner of Jim Davis House’ who clearly does not care about the intervention and seems far more interested in getting people over to her house, which is a party house, because she clearly feels self conscious about blowing all her money on the Jim Davis house. It is perhaps the most surreal and absurd sketch in the entire first season, and it is brilliant.

9. Gift Receipt
I think Tim Robinson’s real talent lies in taking a simple concept and escalating it to absurdity. In this sketch from episode 1, he takes something very familiar, and ripe with real world awkwardness and uncertainty. Gift giving, and goes in the completely opposite direction from where you think the sketch is going. I mentioned up top that one of the ways comedy can be generated is someone at odds with their surroundings, and what I liked most about this one was that Tim’s character wasn’t the crazy person, everyone else was immediately on board, and targeted Steven Yeun’s character Jacob. I’m not sure what I liked most about this sketch, because everyone was on point, and the physical acting and delivery were just superb, but if I had to pick it would be Robinson’s delivery of the line ‘I eat paper all the time’ it was just so funny. 

10. Both Ways
So in this sketch from episode 1 (the very first sketch in fact) we see Robinson’s character finishing up a job interview. It is just so cringingly awkward and much like Brooks Brothers encapsulates the best elements of the show, someone desperately trying to save face or cover up something and going to desperate levels to do so. Overall it’s a really simple premise, it has Robinsons character go to leave after an interview, and pull on a push door, the interviewer politely corrects him and Robinson doubles down saying the door actually goes both ways, and then slowly, desperately forces the door to turn inward, breaking it from the hinges. It works mostly because of Robinsons physical acting, and the almost palpable awkwardness of the whole thing. 

Honourable mentions go to Has This Ever Happened To You, Focus Group and Game Night which I also really enjoyed but didn’t quite make the top 10 list.

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