Actor, producer, writer, musician, and comedian extraordinaire Andy Samberg is one smart goofball. Growing up in Berkeley, California, he met soon-to-be best friends Akiva Schaffer and Jorma Taccone, who were in 8th grade when he was in 7th. In a recent sit down with Collider, the three friends reminisced about what drew them together. High school is where the “venn diagram” of their friend groups met, and the three immediately hit it off and started making comedic music videos and shorts. Taccone says that his first impression of Samberg was that he was “next level funny,” and would do anything for a laugh. As for Andy’s initial thoughts of the other two, it was also an instant connection.

The trio, best known collectively as The Lonely Island, started borrowing cameras and making videos, with “Just 2 Guyz” being one of the first. Things quickly sped up from there, as they went from filming around their neighborhood to writing for 2005’s MTV Movie Awards hosted by Jimmy Fallon. They were so memorable, in fact, that Fallon mentioned their names to his old boss over at Saturday Night Live, the legendary Lorne Michaels. (Check out the fun press junket bit The Lonely Island guys did in 2016 here.) Shortly thereafter, The Lonely Island crew moved across the country and brought their charm and unique comedy voices to SNL. They wrote together and shot together, which they acknowledge is a luxury that most new writers at the show wouldn't have. There were, however, plenty of struggles along the way. Heck, they still didn't have their own cameras. (They borrowed Bill Hader’s then-wife Maggie Carey’s cameras she snagged from the film school she was working at.) The huge, overnight success of their second SNL Digital Short “Lazy Sunday” was just the beginning of their legacy. Their dreams of making movies would also come true, as they were offered the cult-classic Hot Rod their first summer at the show.

Since his 7 stellar years on SNL, Samberg hasn’t stopped acting or collaborating with Schaffer and Taccone. Their production company produces projects such as PEN15, I Think You Should Leave with Tim Robinson, Popstar: Never Stop Never Stopping and the Sundance hit Palm Springs. Additionally, Samberg starred in and produced the NBC series Brooklyn Nine-Nine, which follows the misadventures of Detective Jake Peralta (Andy Samberg) and the other folks that work in the NYPD’s 99th precinct. The show survived several cancellation scares along the way, and recently ended its impressive 8 year run. Whether you love him as Jake, Conner4Real, or Nicolas Cage, nothing can beat Andy Samberg’s early days on SNL and the videos that made him a household name.

There’s so many wonderful Digital Shorts to choose from, yet so little time. Let’s go through some of the funniest and most absurd ones, shall we?

Best Friends

Sometimes all you need is some holiday cheer and your best friend. Someone that will wrap presents with you, go caroling, and of course, watch The Lion King. But what happens if you bump into a “handsome drug addict” (Matt Damon) or a “brilliant lunatic” (Val Kilmer)? Well, then you obviously invite them along for the ride. In this short, Andy Samberg and his best friend (Katy Perry) show how much one’s life can change simply by adding a few more people to the friend group. Blood is shed, songs are sung, and drugs are everywhere. Also in this video: a bird-man hybrid, Marilyn Monroe, and Abraham Lincoln. Glorious.

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D**k in a Box

Giving a gift to that special someone in your life is hard. How are you possibly supposed to sum up all the feelings you have for a person in just one gift? It’s a lot of pressure. Luckily, these two R&B singers (Andy Samberg and Justin Timberlake) believe they’ve come up with the most genius idea: Just put your d**k in a box. It’s pretty simple, but if you’re confused, don’t worry, they explain how to do it in three easy steps. This song became so popular and beloved by fans and critics alike that it won the Emmy for Outstanding Music and Lyrics and received over 25 million views on YouTube. Can’t get enough of these characters? Check out the sequel song parodies, “Motherlover” starring Susan Sarandon and Patricia Clarkson and “3-Way (The Golden Rule)” with Lady Gaga.

Lazy Sunday

Everyone has suffered through the Sunday blues. Maybe you’re dreading school the next day or a meeting at work. A lot of people take Sundays easy and relax before another busy week takes over. All because Sundays tend to be lazy, doesn’t mean they have to be boring. In fact, they can be pretty epic. In this short, Andy Samberg calls up his buddy and fellow castmate Chris Parnell to see if he'd be down to hang out. Not only are they ready to pal around, but they’re ready to rap about it. Some of their shenanigans include eating cupcakes, seeing The Chronicles of Narnia: The Lion, the Witch, and the Wardrobe, and debating which navigation platform is best. (It’s Google Maps. It’s “double true.”) The huge overnight success of “Lazy Sunday” (which was only their second short at the show) cemented their status and set the stage for dozens of shorts in the years to come.

I Broke My Arm

There’s always that person in school who breaks their arm and suddenly gets all the attention as people clamor to sign their cast. In this short, that someone is played by Emma Stone. She struts into the school cafeteria with her backup dancers in tow to explain to her classmates (through song, duh) exactly how she broke said arm: she slipped and fell in grape jelly. As she dances her way through this explanation, however, she slips and falls again, resulting in another broken arm. She repeatedly suffers through this vicious cycle, breaking another bone with every spill. Tired of being blamed for this whole disaster, the grape jelly (Andy Samberg) shares his side of the story. You’ll never look at a peanut butter and jelly sandwich the same way again.

Shy Ronnie

There’s nothing more powerful than knowledge, and Rihanna and Shy Ronnie (Andy Samberg) are here to share that wisdom nugget with a classroom full of kids. Easy enough, right? As expected, Rihanna effortlessly nails her part of the song. But when she throws it over to Shy Ronnie, things get a little dicey. And quiet. Just as his name suggests, Shy Ronnie is really shy and too scared to sing with Rihanna. Instead, he just whispers inaudibly into his microphone. Finally fed up, Rihanna leaves the room, and only then does Shy Ronnie have the confidence to burst into rap.

People Getting Punched in the Face Before Eating

While all the names of the SNL Digital Shorts are pretty revealing, the title of this short, “People Getting Punched in the Face Before Eating,” takes the cake. Just don’t eat the cake in front of Andy Samberg, because, well, he’ll punch you. Whether you’re on a bench, standing outside 30 Rock, or leaving your favorite pizza joint, if you’re eating, you will get punched in the face. Also in this short: Jon Bon Jovi, Dave Grohl, Taylor Hawkins and...zombies? Right, of course.

Great Day

Dennis (Andy Samberg) doesn’t know why, but he thinks it’s going to be a great day. A really great day. Which is quite the positive outlook for a guy who’s house is a mess, recently lost his job, got divorced, and doesn’t hear from his kids. And he has a mysterious white powder under his nose. Nevertheless, Dennis sings in the streets, climbs trees, and listens to the birds sing. But, then he freaks out at his friend, curses out a construction worker, and says that he’s living in the matrix. Oh, wait. He’s on drugs.

Natalie Raps

Oscar winning actress Natalie Portman, known for her incredible performances in projects like Black Swan, Jackie, and Closer, is one of the most composed, elegant, and respected people in the industry. But being a role model for aspiring artists is a lot of pressure and responsibility, and Natalie’s had enough. She’s done pretending she’s this perfect person, and she’s going to let everyone know who she really is. In this black and white short, Natalie Portman trades in her typical dress for a leather jacket, and raps about smoking weed, cheating at Harvard, and admits she’ll kill your dog for fun. Midway through the short, Andy Samberg joins her dressed as a viking and sings along about how badass Natalie can be.

Party at Mr. Bernard’s

Devon (Andy Samberg) and Ricky (Bill Hader) cannot wait to spend the weekend at their boss Mr. Bernard’s (Robert De Niro) sweet beach palace. Whoa, hold on, is Mr. Bernard dead? They should probably call the cops and cancel the big party. Or, they could just dress him up in a Hawaiian shirt and pretend he’s alive. (Sound familiar?) Oh, how could anything possibly go wrong. Well, actually, none of the party goers are fooled at all, especially Kristen Wiig’s character, who throws up in a vase and tells Devon and Ricky they are going to Hell. Inevitably, Devon and Ricky end up in court, where they are surely going to be found guilty of something. Or will they?

Doppelgangers

Just three guys (Seth Meyers, Andy Samberg, and Will Forte) wearing wrinkled dress shirts and eating sandwiches on their lunch break. But, wait, hold on a second. Doesn’t that guy with the mustache look like Will Forte’s doppelganger? And the other guy standing against the wall in the top hat...he looks exactly like Seth Meyers. Now all Seth and Will have to do is find Andy’s uncanny look-alike. Much to Andy’s horror, his two work buddies think his doppelganger is the weird guy (Horatio Sanz) hanging around the garbage. Andy decides to put this crazy notion to bed, and stands right next to the stranger to prove how they don’t resemble each other. Will his friends be able to tell them apart?

Helen Mirren’s Magical Bosom

Everyone knows that Helen Mirren is a fantastic actress and a true Hollywood legend. What a lot of people might not know is that she’s also magic. To be more specific, she has a magical bosom. Cast member Nasim Pedrad gently knocks on host Helen Mirren’s dressing room door and asks if she could, well, touch ‘em. When Helen grants Nasim’s wish, Nasim is transported through time, reliving events like the moon landing, the O.J. trial, and the Oslo Accords. Then she lands not in Heaven, but in a place above the clouds that is much better than Heaven. Just let Andy Samberg’s god-like character explain.

YOLO

Though Andy Samberg left SNL in 2012, that doesn’t mean the Digital Shorts we love are no longer. In “YOLO,” a surprise short from Season 38, Andy sings about how precious life is and in turn, how careful we must be. That’s right, The Lonely Island boys are back and they brought along their vocal chords, Adam Levine, and Kendrick Lamar. Some might think the acronym “YOLO” means “you only live once,” but these guys are here to explain that it actually means “you oughta look out.” Since in fact you only live once, be sure to take all the proper precautions: don’t use saunas, don’t go to loud clubs, do drugs, or take the stairs. And beware of couches, kids’ hair, and make sure to pull out all of your teeth. Is that a piano? Look out!

That’s When You Break

We’re closing out this deep dive into absurdity with a heartfelt tribute to all the times that Saturday Night Live cast members couldn’t hold it together. At the epic 40th anniversary special, Zach Galifianakis introduced a Digital Short starring Andy Samberg and Adam Sandler singing and strumming guitars as they look back at the times when the cast broke character. Some of the clips included laughs over the years from Kristen Wiig, Norm Macdonald, Will Ferrell, Chris Rock, Gilda Radner, and Chris Farley. (And, of course, Jimmy Fallon.) This lovely montage is sure to leave tears in your eyes.

You probably still have a Samberg-shaped whole in your heart, but never fear. You can find him co-hosting the upcoming competition series Baking It! with Maya Rudolph and you can stream Brooklyn Nine-Nine on Hulu.

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