Getting your questions ready
Getting your questions ready
Beat the crowd
10 questions No timer
50 free I Think You Should Leave trivia questions with answers — entertainment quiz, new questions added Aug 2026.
I Think You Should Leave with Tim Robinson turned three short Netflix seasons into one of the most quoted comedies of its era. This quiz covers all 18 episodes: the sketches, the characters, the guest stars, and the people who made it (Tim Robinson, Zach Kanin, director Alice Mathias and The Lonely Island). Expect questions on the hot dog car, the Focus Group, TC Tuggers, Coffin Flop, Karl Havoc, Dan Flashes, sloppy steaks, Detective Crashmore, Calico Cut Pants, the Driving Crooner and the 55 burgers order, alongside real-world facts: which awards it won, when each season dropped, who Biff Wiff and Ruben Rabasa are, and what Robinson did before the show. Easy questions warm you up; the hard ones require remembering which sketch sits in which episode. Every answer was checked against Netflix's own sketch guide or an encyclopaedic source before publishing, so the score you share will hold up.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Who co-created I Think You Should Leave with Tim Robinson?
Zach Kanin
Robinson and Kanin met as writers on Saturday Night Live and previously made Detroiters together.
Q 02On which streaming service did I Think You Should Leave premiere in 2019?
Netflix
The first season landed on April 23, 2019.
Q 03Which comedy trio serve as executive producers on the series?
The Lonely Island
Andy Samberg, Akiva Schaffer and Jorma Taccone; Schaffer also co-directs most episodes.
Q 04Which director co-directed most episodes with Akiva Schaffer and called it 'unhinged'?
Alice Mathias
An episode she directed, 'Has This Ever Happened to You?', made IndieWire's best TV episodes of 2019.
Q 05Season two's release was delayed by what?
The COVID-19 pandemic
It was renewed in June 2019 but didn't arrive until July 6, 2021.
Q 06In which year did season three premiere?
2023
Netflix announced the renewal in May 2022; the six episodes arrived on May 30, 2023.
Q 07Which Primetime Emmy did Tim Robinson win in both 2022 and 2023 for the show?
Outstanding Actor in a Short Form Comedy or Drama Series
The show itself won Outstanding Short Form Comedy, Drama or Variety Series in 2023.
Q 08On which series did Tim Robinson unusually move from cast member to staff writer?
Saturday Night Live
He was only the second cast member ever, after Brian Doyle-Murray, to make that switch.
Q 09Which Comedy Central sitcom did Robinson and Sam Richardson co-create before I Think You Should Leave?
Detroiters
They play struggling ad men making local TV commercials in their real hometown.
Q 10Which US city is Tim Robinson from?
Detroit
He got his start at the Second City's branch there before joining Second City Chicago.
Q 11The Season 1 sketch 'Focus Group' made a star of which octogenarian actor?
Ruben Rabasa
He is Focus Group Man #1, the one with strong opinions about steering wheels and his son-in-law.
Q 12The Season 1 'Focus Group' sketch is about a panel discussing what product?
A car
One panelist has a very good idea: a steering wheel that doesn't fly off while you're driving.
Q 13In the Season 1 sketch 'Brooks Brothers', what kind of vehicle has crashed into the store?
A hot dog car
The man in the hot dog suit insists 'we're all trying to find the guy who did this'.
Q 21Which Season 1 sketch features an office thanking a certain visitor from the North Pole?
New Printer
Season one's Santa is a coworker who is definitely not the real thing.
Q 22Which sketch closes Season 1 with an intervention?
Party House
The intervention is staged in a house that has, let's say, seen some parties.
Q 23Coffin Flop, the show of real people falling out of coffins, airs on which fictional channel?
Corncob TV
The channel head protests Spectrum dropping his channel.
Q 24Karl Havoc hosts what kind of programme in a Season 2 sketch?
Q 14TC Tuggers, advertised in the sketch 'River Mountain High', is a shirt with what unique feature?
A tugging knob
The commercials interrupt a fake high-school drama that the shirt sponsors.
Q 15In the Season 1 sketch 'Gift Receipt', what does the gift-giver do after asking for his receipt back?
Swallows it
He then insists the gift cost far more than it actually did.
Q 16The Season 1 sketch 'Baby of the Year' is about what kind of competition?
A cuteness contest for infants
The audience turns viciously on a baby named Bart Harley Jarvis.
Q 17Which jazz legend receives a lifetime achievement award in a Season 1 sketch?
Herbie Hancock
The presenter's tribute goes badly off the rails.
Q 18In the Season 1 sketch 'Traffic', what triggers the road incident?
A bumper sticker
It ends with a eulogy for the concept of 'Friday Night'.
Q 19What is 'Chunky' in the Season 1 sketch of that name?
A game show mascot
He steals the spotlight from the actual contestants.
Q 20Which actor plays the music executive in the sketch 'The Day Robert Palins Murdered Me'?
Rhys Coiro
The sketch became one of the series' most recognised, and it's a musical.
A hidden-camera series
His prosthetics go awry and he decides he doesn't even want to be around anymore.
Q 25What does the store Dan Flashes sell?
Patterned shirts
The more complicated the pattern, the more it costs, and rightfully so.
Q 26In the Season 2 sketch 'Baby Cries', the man holding a crying baby is trying to enjoy what?
A sloppy steak
His past involves sloppy steaks at Truffoni's, and he's determined to change.
Q 27Who plays the man who suspects a baby is aware of his checkered past in Season 2?
Bob Odenkirk
Odenkirk delivers the pitch for sloppy steaks with a creepy wink.
Q 28Detective Crashmore, star of the fake action film trailer, is played in-universe by whom?
Santa Claus
Biff Wiff played the profane Santa; the sketch launched his late-life career.
Q 29Which real film does Biff Wiff appear in after his breakout as Santa on the show?
Everything Everywhere All at Once
He played Rick, and later Steve in the reality-hoax sitcom Jury Duty.
Q 30The 'H.D. Vac' is a vacuum designed to suck what out of a person?
Hot dogs
The commercial spokesman speaks from personal experience.