Two very important things happened on April 23, 2019. One: Damian Lillard hit one of the most audacious shots in NBA postseason history, waving goodbye to the Oklahoma City Thunder as we knew them and unknowingly greasing the wheels on two of the most jaw-dropping trades of the NBA’s stunning summer. Two: I Think You Should Leave With Tim Robinson, a brilliant and bizarre sketch-comedy blitz created by Saturday Night Live alums Robinson and Zach Kanin, premiered on Netflix.
If you’re the kind of person who breathlessly celebrated both occurrences, you’re precisely the target demo for I Think You Should League Pass (@nbaleave)—a Twitter account dedicated solely to humor aiming for the center of the Venn diagram between NBA obsessives and “You have no good car ideas” devotees. And if you’re an NBA fan with no idea what I’m talking about ... well, you should probably find out (I Think You Should Leave is one of the funniest shows of the year), but the specificity of the basketball jokes will probably have you laughing along even if you’re not familiar with the context of the references from the show.
You’d probably also enjoy talking to Ryan Perry. After all, the New Jersey–based editor is the man behind the memes.
Once upon a time, Perry described himself as a “serial entrepreneur,” a guy who would start independent blogs—like the celebrity gossip site What Would Tyler Durden Do?, sports site With Leather, and movie site FilmDrunk—and sell them off to other companies. After Uproxx Media acquired With Leather and FilmDrunk in 2008, Perry joined the company as its creative director. (“It was kind of like an acqui-hire situation,” he said.) Since March 2018, Perry, 37, has been the engagement editor at Popular Science, running the magazine’s social media feeds and helming some of its audience development initiatives.
For the better part of the last 15 years, as he describes it, Perry’s job has been to be “just extremely online.” That’s probably why the idea of a meme marriage between his loves of the NBA (which he traces back to his youth as a fan of the Shawn Kemp–and–Gary Payton–led SuperSonics) and I Think You Should Leave (which he said “completely poisoned my brain from the first minute we turned it on”) occurred so naturally to him.
“I’m in a group chat with some old work friends, and we’re constantly quoting the show,” he said. “And then, around the time of the NBA draft ... I shot off a tweet from my personal account,” Perry said. “I memed—you know the Johnny Cash parody sketch?”
Yes, I did. If you don’t, please enjoy.
OK. Back to the interview.
“So I labeled Tim Robinson’s character ‘Woj’ and then I labeled the other character ‘NBA draft TV broadcast,’ because he’s always preempting all of their scoops and stuff like that,” Perry said. “And I tweeted that from my personal account, and it got some attention.
“And then I kept thinking of other crossover ideas I’d like to tweet from my personal account, but it just felt very niche. So I went into that group chat I have with my friends. I was like, ‘Hey, should I just start a separate crossover meme account?’ And they were supportive of the idea.”
Three weeks later, Perry launched I Think You Should League Pass and began exploring how he could tie Robinson’s absurdist comedy (which has ventured into the basketball world in the past!) to the NBA news of the day. It was … shockingly easy?
“If I didn’t have this account, I’d probably just be shouting these references at the TV,” Perry said.
Despite that passion, even those who shared Perry’s enthusiasm for the project figured it wasn’t long for this world. “My friend Brian Grubb, who’s a writer for Uproxx and was part of that conversation where he was very supportive about starting the account, he said, ‘Yeah, I really didn’t see this lasting more than a week or two,’” Perry said.
Grubb confirmed his skepticism. “I thought it was a great idea and I had no clue how he would pull it off,” he told me via Twitter. But nearly five months later, the account is still going strong, with more than 14,000 followers and each day offering some inspiration for another crossover joke.
“I think it’s just a testament to [the fact that] there’s really an audience for everything,” Perry said. “The NBA has such rabid fans and the show has such rabid fans, I guess it was kind of inevitable that if it was produced correctly, a crossover would find some space in that Venn diagram.”
He has also returned to certain I Think You Should Leave characters and moments often. (As you might expect, given that the show thus far consists of just six episodes, 29 sketches, and just over 100 minutes of total material.) He seems particularly fond of the hot-dog-costume-clad weirdo Robinson plays in the sketch that opens the show’s fifth episode:
“The hot dog guy is a moron, and he doesn’t realize that he’s a moron, and I think there’s a lot of characters like that in the sports world and the online world,” Perry said. “It’s also pretty hilarious that he’s also calling out other people for being morons, you know?”
No, I certainly don’t. It’s not like I have spent a crushingly embarrassing amount of time over the past decade arguing about who’s over/under/properly rated on Basketball Twitter, or anything like that.
Five months in, Perry’s still enjoying the challenge of mining the league and show for fresh comedy gold. His personal favorite veered off the court completely, using screenshots of Robinson stopping to drink water to illustrate the pregnant pause that ESPN’s Zach Lowe takes after saying “Welcome TO!” in the introduction of each episode of his podcast.
“I was like, I don’t care if people don’t get this. I don’t care if it gets zero engagement. I’m doing it because it makes me laugh,” Perry said. “And I’ve had people DM me saying, ‘I felt like this tweet was specifically for me.’ And that’s just weirdly gratifying to me.”
He keeps finding character parallels, identifying Chris Paul as the NBA’s answer to the star of the “Focus Group” sketch: “He goes back and forth between joking with people, but then all of a sudden he can turn on a dime and be nasty.” Picking out a “Baby of the Year” is a bit trickier. Perry notes that Raymond Felton “is the closest thing the NBA’s had to that ‘99th percentile in weight, 10th percentile in height’ chode range the judges love,” and “doesn’t have a flat back of the head, like that piece of shit Bart Harley Jarvis.” As Felton remains unsigned and off an NBA roster, though, he might not technically qualify.
Other riddles persist. Perry’s still searching for the perfect match for “the very last sketch in the show—the one that’s the Jim Davis house, the Garfield house.” As it turns out, it is not easy to find the proper NBA entry point into a scene built around three friends staging an intervention for a fourth … in a bright orange living room in which, apropos of nothing, all of the decorations and furnishings look like Garfield, Odie, or Nermal. Perry senses that Dwight Howard should be involved, but he hasn’t locked in on that yet. The calculations continue.
As he works on cracking those hard cases, Perry will remain extremely online and extremely into the ever-roiling soap opera that is the NBA—which is to say, the well doesn’t seem likely to run dry any time soon. I Think You Should Leave’s second season will be here before you know it, and until it arrives, Perry can lean on some of the league’s more reliable sources of joke fodder.
“Well, it’s always easy to make fun of the Knicks,” he said with a laugh. “My philosophy on this is that any level-headed basketball fan knows that there are things about their team or their ownership or their players that are worthy of being made fun of, and they don’t take it personal. So everything’s a target and they shouldn’t take it personal. Except for, obviously, Knicks management. They should read all the jokes, and they should take them all very, very personally.”