Harvard wasn’t part of Benito Skinner’s college experience, he actually went to Georgetown, but this fall he finally gave himself the campus tour he never got. The comedian and actor touched down in Cambridge at the invitation of the PRIDE leaders at Harvard Business School, where he spoke with students about his path from internet breakout to Hollywood multi-hyphenate—and creator of Amazon’s buzzy series Overcompensating, already renewed for a second season, which he’s in the middle of writing. “I just turned in another draft,” he says. “So we’re cooking.”

What began as a simple campus visit quickly snowballed. There was a heart-to-heart with MBA students, a 9 A.M. improv session, and a surreal induction into The Harvard Lampoon—the legendary humor institution that has housed everyone from Conan O’Brien to B.J. Novak. For Skinner, who once felt too closeted in college to fully put himself out there, stepping inside the Lampoon felt like, as he puts it, “a nice full-circle moment, because I really restricted myself in college. I didn’t put myself out there. I was still in the closet and scared to be myself in any way.”

And if you’re going to live out a Legally Blonde fantasy on the Harvard campus, why not dress the part? With stylist Jake Sammis, Skinner leaned all the way into Ivy League Americana, cycling through four Ralph Lauren looks—which is, you know, “a casual day on campus”—to full prep regalia for the Head of the Charles Regatta, that annual collision of rowers, fans, and aggressively preppy outerwear. “When you watch season two, you’ll understand a lot of the things I was observing while I was there.”

But beneath the tweed and ties, the trip doubled as something else: research. Raw material. Homework for season two of Overcompensating. In the conversation ahead, Skinner teases new love interests for Benny, Grace, and one previously unlucky-in-love character; hints that “no one is doing what they did in season one”; and even reveals that he’s been dropping episode titles on social media (spoiler: one is called “Oops… I Did It Again,” with a soundtrack to match the nostalgic college vibe of season one).

Call it homework, call it method research, but when Overcompensating returns, fans may recognize more than a few Easter eggs from one very overdressed weekend in Cambridge.

VMAN: You made it to Harvard! What about this trip felt like a “yes” to you? 

Benito Skinner: The PRIDE leader group for Harvard Business School reached out to me and said, “Would you be interested in speaking to a business class?” And I was like, okay—little me would absolutely love to. Also, we’ve been in the writers’ room, so any opportunity to get on a college campus felt like it would be such a perfect way to get some nice creative juices flowing. I knew the room was going to be full of people who were maybe looking to enter entertainment, or were just fans of the show, or just wanted to talk about my path—from Internet work into stand-up, into creating a pilot and developing a show and pitching it. It was an honor. It was truly insane. I’m an absolute bimbo, so it meant the world. And Georgetown’s been really quiet, so I was kind of like, shit, I’ve got to make them jealous.

And it also happened that we were writing season two of Overcompensating, and I got invited to go see some other clubs, and Head of the Charles was going on that same weekend. So it just felt like the perfect little opportunity to go to Cambridge—which is beautiful—and meet some students. And it really did result in so many new pitches the Monday after with the writers’ room.

I just had the best time. It was like an hour-and-a-half conversation with this group of business students, which was nice because sometimes college students are just kind of staring at you. They don’t really interact, and you’re kind of like, “Am I bombing?” But everyone there—we were kind of the same age—so that was really helpful. It just felt very in-conversation.

And then I got to—actually, I think technically—I’ve been inducted into the Harvard Lampoon, but I don’t know if that’s exactly the term. There are a lot of rules on campus over at Harvard. But that was just so surreal and so fun. And I did improv at 9 AM on a Sunday morning, which is not totally my choice for a Sunday morning, but in the end, I just had the best time. They’re all brilliant, and I’m sure many of them will be in writers’ rooms very soon.

VMAN: When you think of Harvard, what’s the first image that pops into your mind?

BS: Well, Legally Blonde, obviously—which is such a comp for Overcompensating in so many ways. Like, I grew up with that. Cruel Intentions, Clueless—this kind of bubbly Americana, a kind of delicious sweetness. Yet there’s still a grittiness to those stories and redemption arcs, and very human and emotional stories.

And then Good Will Hunting, obviously. Are you kidding? Robin Williams—huge for me. 

VMAN: The Harvard Lampoon has a long history with comedy icons, including figures like Conan O’Brien and B. J. Novak. What does being named an honorary member mean to you?

BS: I’m so honored. It felt like a nice full-circle moment because I really restricted myself in college. I didn’t really do anything aside from making videos on the internet, but I didn’t put myself out there. I was still in the closet and really scared to be myself in any way.

Sometimes it’s what I think a lot of us feel in making the show, which is that we almost get to rewrite some of these things, or re-experience them, and forgive ourselves for maybe some of the choices we made or the things we missed out on. It felt a little bit like that, which I thought was really beautiful. It also meant a lot to my parents. I gave my dad the tie. 

VMAN: If the Harvard Lampoon were to induct one character from Overcompensating, who would it be?

BS: Oh my God, probably Carmen. I think Carmen’s the funniest, naturally, in the show, because Hailee would never try to join that—let’s be real. She’d be like, “Fuck no,” unless it had more prestige and was more front-facing.

When I watch the show back, Carmen always stands out to me. And she’s always fun to write because she’s so sharp and is a writer in the show. Also, Wally was there a month before me. So, true to form, Carmen is already inducted.

VMAN: You visited the Head of the Charles Regatta. What was your fashion plan for the day?

BS: I’m so glad you brought this up. Okay, so Jake Sammis was my stylist for the trip. We decided that we were going to do Ralph Lauren, so we did four looks—which is, you know, a casual day on campus.

But for Head of the Charles, I wanted to give full prep. We might be a TA, we might be a professor, but we might also be a student—you don’t know. I will say, I think I was maybe a little overdressed for Head of the Charles, but I’m happier to be that than underdressed. I had to really step it up for my guys—my guys and girls.

I threw my tie on, my little Oxford shirt, my little pleated pants, and we hit the freaking ground running. And I got to go to the crew facility for Harvard, which was really fun. I can’t believe how tall rowers are. That’s something that really sticks with me. That’s my big statement of the day. I think when you watch season two, you’ll understand a lot of things I was observing while I was there.

VMAN: Did anything surprise you about crew culture?

BS: Oh my God—aside from them being beasts, I think how intense it is out on the water surprised me. You may think it’s peaceful, and they’re just rowing, and there’s a meditative vibe to it—and I do think it has that. But also, I was watching and I was just like, holy shit, they are going. They’re going at it. They’re going crazy. And so are the crowds.

I grew up in football world, so I kind of assumed that every other sport was just a little bit less psychotic than that, because that feels like the pinnacle of everyone being a lunatic. But no—people can get just as intense about rowing.

VMAN: You’ve already been teasing the answer to my next question a little bit throughout the conversation… but with a second season of Overcompensating currently being worked on, did being on campus make you reflect on the future of any of the characters? Is there anything you can tease about what to expect from the upcoming season?

BS: Benny has a new love interest. And so does Grace. And so does a character that hasn’t had one yet. And I would say we’re in new arenas. No one is doing the same thing they did in season one. We have completely new groups and families and everything. It’s like we’ve gone off the trajectories we were on.

I think this trip was also about me sourcing material and thinking about these communities that people join on campuses. And I think you’re going to see that a lot of our characters are joining ones maybe you wouldn’t have thought they would join—including my character.

But it’s been so much fun to write. I just turned in another draft, so we’re cooking. Everyone’s like—if I’m anywhere—they yell at me. They’re like, “Get home and write!” And I’m like, “I swear to God, I’m writing all day. I fucking promise this season is getting written. I just have to eat dinner.”

I’ve been teasing some of the names of the episodes on social media. One is “Oops… I Did It Again.” The music is… I would say it’s even more of that college nostalgic vibe you got from season one. We’re really pushing up the season.

VMAN: To wrap it all up, what advice would you give to someone still in college who is interested in pursuing a career in film and television? 

BS: I feel like I would tell them: you just have to do it. Don’t limit yourself based on—like I did for so long—thinking, “I don’t think I’m a comedian.” And then I remember one day I was with Mary Beth Barone, and she was like, “You’re doing a stand-up show. Your name is on the marquee. You’re a comedian, freak. Like, stop.”

You don’t have to have these things in your head—these iron gates of the industry, or the idea that you have to have gone to school to study acting or writing or filmmaking. We have phones and Notes apps in our pockets. You can write scripts, and you can make sketches and shorts.

And I think that’s what did it for me—I just did it. And I made a lot of things that I now think are not funny or not that great, but it got me to a place where I could find my comedic voice and the voice I wanted to have as a writer. To the point now where, in writing season two, I realized how much I found that voice through all that time spent just doing it.

Honestly, just get your head down and do the work. Because if you love the work, doing all that will be enjoyable as well—even if later you get reminded of a sketch you did on TikTok and you’re like, “That is so bad. Let that one fucking die.”

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Photography Maddy Rotman

Fashion Jake Sammis