Happy Birthday to Andy Samberg, the Least Disappointing Man In Hollywood

My introduction to Andy Samberg—who turns 42 today—was in 2009 via the annoying guys who sat in the back of my math class. They wouldn’t stop watching “I’m On a Boat” on their phones and singing along at the top of their lungs, and were eventually given detention. Suffice to say, it wasn’t a great first impression of a comedian who I assumed was as irritating and offensive as the boys who loved him.

But after school, when I watched the video that had made such a fuss, I was surprised to find I wasn’t disappointed. Though I wasn’t entirely sure the guys from my class realized it, it was obvious the video was making fun of the macho, dude-bro attitude that comes with saying, “Take a good hard look at the motherf*cking boat.” Over 100 Saturday Night Live digital shorts, three movies, one TV show, and one live concert event later, and I’m one of Samberg’s biggest fans.

Today is Samberg’s 42nd birthday, which means he has made it to the age of 42 without disappointing me. The secret, I think, to Samberg’s success is he and his writing partners, Jorma Taccone and Akiva Schaffer, have always been ruthlessly mocking the characters they play. They would say they are making fun of themselves—that was essentially the thesis of Samberg’s recent profile in GQ magazine, in which Samberg said The Lonely Island‘s No. 1 rule was to “always be the butt of the joke”—but that’s not quite right.  After all, Samberg’s characters are rarely liberal guys from Berkeley, California who graduated from Tisch and married an internationally renowned harpist. They’re dude-bros who brag about being on boats, creeps who give their girlfriends their dick in a box for Christmas, and they’re narcissistic pop stars who take a dump in the Anne Frank House.

By the time Popstar: Never Stop Never Stopping rolled around in 2016, most people had caught on that Samberg’s exaggerated version of Justin Bieber was decidedly not a compliment. But back in 2009 when “I’m On a Boat” went viral, Samberg accrued a lot of fans who would be singing that song while slamming beers on their parent’s boat unironically. I’m still disappointed that a similarly aggressive fake rap song The Lonely Island put out two years later, “We’re Back,” never draw as much attention, perhaps because anyone who tried to rap along would be forced say, “Yo my dick don’t work, that sh*t is soft as a pillow.”

In 2013, when The Lonely Island released the music video for “Spring Break Anthem,” Samberg went out of his way to make his intentions clear. In an interview with Pitchfork, he explained the song was intended to point out “how so many of the macho, aggro dudes who have such a problem with gay marriage have no problems with acting like fucking animals on spring break.” (The video came out two years before same-sex marriage was legalized by the Supreme Court.) Three years later, Samberg turned that ire on “straight ally” dudes like Macklemore with “Equal Rights,” a song in which Connor4Real spends more time insisting that he’s straight than he does advocating for gay rights.

Most recently Samberg produced and starred in the Hulu film, Palm Springs. It feels less like an Andy Samberg character, and more like an Andy Samberg role. He didn’t write the script, for one, which is about nihilistic wedding guest caught in a Groundhog Day-esque time loop who falls in love with the maid-of-honor (Cristin Milioti) when she, too, is caught in the loop. Perhaps some were surprised by the heartfelt, romantic tone of the film after years of Samberg’s fake rap persona. Others might be surprised that he consistently says things that are smart, progressive, and thoughtful when he does press tours, like when he said that he thought that the Guy’s Choice Awards were stupid on the red carpet for the Guy’s Choice Awards. But the truth is, Samberg has always been a feminist—a word many of his early fans likely use as an insult to this day.

I get it. Other white male comedians have set a depressingly low bar. But if you’d been paying attention all along, you wouldn’t be surprised at all to learn that Andy Samberg isn’t disappointing. Well, unless you’re one of those guys from my math class. They might feel a bit let down.

Where to watch Popstar: Never Stop Never Stopping