‘I Think You Should Leave’ Sets Season Two Premiere with Season One Wrap-Up Song

In lieu of a trailer teasing the antics fans can expect from Tim Robinson (Detroiters, Saturday Night Live) and the I Think You Should Leave crew in the upcoming second season, Netflix dropped a video of Robinson singing a mash-up of references from season one’s collection of sketches. Sam Richardson (Detroiters, Veep) joins Robinson’s song, which Collider describes as “an appropriately weird reminder of the show’s musical numbers.” Along with the medley came the news that the second season of I Think You Should Leave will be hitting Netflix on July 6.

The sketch comedy series first premiered on Netflix in 2019, with Saturday Night Live alum Robinson at the helm, and was flooded with veteran comedy talent both on-screen and behind-the-scenes. Current and former Saturday Night Live players Vanessa Bayer (Trainwreck, Office Christmas Party), Will Forte (The Last Man on Earth, Nebraska), Cecily Strong (Ghostbusters, The Awesomes), and Andy Samberg (Brooklyn Nine-Nine, Palm Springs) all made cameos in sketches, with Samberg’s production company likewise involved in the series. Samberg’s The Lonely Island colleague Akiva Schaffer (Saturday Night Live, Popstar: Never Stop Never Stopping) directed a season one episode of I Think You Should Leave, as did Portlandia’s Alice Mathias (Documentary Now!, Shrill). Additional season one guest stars included Richardson, Steven Yeun (Minari, The Walking Dead), Tim Heidecker (Tim and Eric Awesome Show, Great Job!, Us) and the late Fred Willard (Best in Show, Anchorman: The Legend of Ron Burgundy).

Opting for an announcement video that is musical mash-up of season one, the I Think You Should Leave crew did not provide any indication as to what new or returning guest stars could be expected in the show’s second season. Collider notes that Richardson’s presence in the wrap-up song serves as a sign that he will be returning. As Richardson is a long-time collaborator and friend of Robinson, many fans might have suspected his inclusion in season two of I Think You Should leave as a given already.

Robinson and Richardson are accompanied in their medley – put out by Netflix’s comedy account Netflix is a Joke – by musician Phredley Brown. The A.V. Club denotes the order of season one songs covered in the video as “Friday Night,” “Baby Of The Year,” “Moon River Rock,” and “Palm Tree Girls,” pointing out that the version of “Palm Tree Girls” included is a longer version than the one in the season one sketch. Of course, Christmas came early when Robinson and Richardson rounded out their medley with a version of “Up on the Housetop.”

As with many other series, I Think You Should Leave’s season two production was delayed by the COVID-19 pandemic. However, in the longer wait between seasons, the series has “garnered a cult following, with more and more people discovering the bizarre brilliance” (Entertainment Weekly).

The wait is almost over for I Think You Should Leave fans, with the series officially set to return to Netflix on July 6. While Robinson’s clever version of a trailer/announcement served up the greatest hits from season one, it obfuscated a glimpse into the show’s second season, beyond tone. Perhaps, in the coming month, an official trailer or teaser will be provided to give fans an official look into the season.

Tara McCauley: A freelance writer and editor fueled by caffeine and an abiding passion for all things television. Studied Communications and Film on the East Coast before moving to Los Angeles to pursue a career in the creative arts. Hobbies include live music and Dungeons & Dragons.
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