The 15 Best Lonely Island Videos

Popstar Never Stop Never Stopping Andy Samberg Lonely Island

Hip hop and comedy have never come together so good.

The hip hop parody group known as the Lonely Island has been make side-splitting digital shorts for well over a decade now, making songs that are gut-bustingly funny while still being unbelievably catchy. Comprised of comedians Andy Samberg, Akiva Schaffe and Jorma Taccone, the group formed in junior high, where the trio met, and they began making low budget short films after college. They struck gold when they were all hired on Saturday Night Live, Schaffe and Taccone as writers with Samberg as a regular player. They gained huge fame on the sketch show by using their own brand of humor to create their Digital Shorts, online videos that often became viral juggernauts.

While they no longer write or perform on SNL, the Lonely Island are far from disappearing from the limelight. They've enjoyed commercial success from 3 studio albums, made a feature length film Hot Rod, and have even been nominated for a Grammy. This weekend they'll be further adding on to their impressive resume with their film Popstar: Never Stop Never Stopping, a mockumentary about fictional pop sensation Connor 4real, who isn't exactly the most socially conscious musician.

In celebration, we're taking a look back at the group's goofiest highlights throughout the years. Here are the 15 Best Lonely Island Videos.

***WARNING: If you're unaware of the Lonely Island's usual output, some of the language and subject matter is, uh, very adult. Proceed at your own discretion.***

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15 Like a Boss

The word “boss” has been thrown around so many times in hip hop music that it’s very meaning has become jumbled. To phrase it just correctly, being a “boss” is to be in employment of oneself. You are in charge of your own situation. Hip hop moguls are fond of being “bosses” because they act outside of the system; they bend or conform to no one’s will.

A proverbial play on the word itself, the Lonely Island takes the meaning of “boss” quite literally here. Samberg, as a low-level manager, attends a performance report meaning with his superior, played by Seth Rogan. When questioned about how the branch manager spends his days as a boss, Samberg goes down the list which includes mundane activities like approving memos, talking to corporate, and hitting on fellow employee Debrah. As the list goes on the activities become more outlandish, which include chopping his own genitalia off, crashing his car, and puking on Debrah’s desk.

Parodying hip hop's cultural significance of the word, Samberg’s routine and otherwise hardcore lifestyle is just another life in the day of the “baus.”

14 J*** in My Pants

The remarkable thing about the Lonely Island is they can take something completely weird, like oh, say, premature ejaculation, and at the same time craft a remarkably catchy pop song about it. “Jizz in My Pants” is the trio’s ultra-catchy electronic single about premature ejaculation. Samberg and Jorma break out into faux English voices as they “j*** in their pants” resulting from talking to beautiful women, listening to music, and even from just having a breeze blow across their lap.

The number is an obvious dig about guys who are completely insecure about, um, blowing their load far too early. It’s also a slight wakeup call to the ramifications that this insecurity has on the opposite sex. After firing off too quickly, Samberg sings to the woman he has taken home, “don’t tell your friends or I’ll call you a slut,” a funny yet stark realization about how insecure guys will blame women for their inability to perform between the sheets. Or in Jorma's case, blowing his load in the checkout aisle in the supermarket.

13 Natalie Portman's Rap

Respectful, lovely, and a national treasure, Natalie Portman is a squeaky clean celebrity that is adored by the masses. Or so it would have seemed before this SNL Digital Short was released, which featured the actress is her absolute filthiest, raunchiest, and all around most hardcore. While being interviewed by frequent Lonely Island collaborator Chris Parnell, the actress lets rip about her gangster lifestyle, which includes drinking, taking drugs, beating people up, cheating on tests, and slapping young fans when asking for an autograph.

A graduate of Harvard and an Academy Award Winner, Portman was ripe for satirization, and who better to do it than Natalie Portman herself? The rap is absolutely hilarious as the actress dives into her violent and hedonistic lifestyle. Sometimes the Lonely Island are not above doing things just for shock value, and this is one of those times that it absolutely works.

12 Just 2 Guys

One of their earlier works, “Just 2 Guys” is the video that earned the comedy trio their writing gigs on SNL. Shot on a miniscule budget of almost $0.00, the purposely dorky music video stars Akiva and Jorma as two guys who awkwardly meet at a party, with no one else there, and proceed to have a good time together.

Jabbing fun at people who are socially awkward, and perhaps to some degree themselves (the 2 pull off awkward so good here), their deadpan humor is on full blast as the Lonely Islanders chill in hilarious swim trunks and pretend to be tough when we know they’re anything but. As they describe it, it’s a friend thing; just 2 friends hanging in the kitchen, the den, and on the stairs. While “Just 2 Guys” only features Akiva and Jorma, Andy Samberg manages to pop his head in halfway through the sketch, and is then hilariously asked by his fellow members, “Who invited that guy?”

11 When Will the Bass Drop?

When will the bass drop? That’s the question on everybody’s minds as they eagerly await the hottest DJ on the planet, Davvincii, to finally get the club jumping. After some group chanting, Davvincii (played by Samberg) pops up from his DJ booth and starts the beat. It’s nothing but pure buildup for 2 minutes straight, but the overzealous crowd can’t get enough of it. The anticipation is all we can take as we watch Davvincii play computer games, fry an egg, play with his finger-skateboard, take a log out of Jenga, and even recover from a fatal heart attack before he lets that bass drop.

The video is an obvious dig at club DJs who obviously don’t have to do much to perform their jobs. Everything here is total parody, including the stereotypical electronic music, the insanely over-the-top crowd (“He’s the King!”), and even Samberg’s name, which is haphazardly taken from a famous 15th century inventor and mangled with actual DJ Avicii. Spoiler alert: Davvincii finally lets that bass drop, but it may not be what you were expecting.

10 Motherlover

God only knows what Andy Samberg and Justin Timberlake were talking about when they stumbled onto this idea for a music video. Straight off the success from another gem on this list, the duo reteam for this, uh, let’s call it Mother’s Day song. After finding out that neither of them have gotten anything for their moms for Mother’s Day, they decide that what their maternal guardians really need is a man. They agree to make a “switcharoo” and hook up with each other’s moms, which they put to the tune of some classic '90s R&B sounds.

It’s both freakishly uncomfortable and rowdily funny as we watch Timberlake and Samberg parade around each other’s moms doing sexy poses, and singing about doing the deed. Their cliché 90s personas are the icing on the cake, and once again Lonely Island makes a song that’s downright goofy and mind numbingly catchy. So much so that you’ll probably find yourself singing along to the lyrics, which include, “They will be so surprised, we are so cool and thoughtful/Can’t wait to pork your mom, I’ll be the syrup she can be my waffle.”

9 Spring Break Anthem

This Lonely Island affair starts like any MTV hyper-masculine music video at spring break. Beer bongs, hot chicks, shot glasses and frat kids running around having a blast are all present. As the Islanders sing about partying it up at Spring Break, a lyric suddenly cuts in that throws off the whole song, “marry a man.” Shots are then intercut between the frat boys living it up, and their future selves vowing their eternal love to another man, which in their case is Edward Norton, Zach Galifianakis and James Franco.

By splicing together imagery from both settings (Spring Break and a gay wedding), the Lonely Island shows which is the more psychologically harmful. The trio chronicles the rather venomous nature of bro culture by juxtaposing it with something that's still taboo to some members of society. This in turn makes the viewer realize that while gay marriage is still looked at as culturally taboo to some, it is completely harmless, especially when compared to Spring Break, which has guys “making jokes about roofies” and “pounding some brews.” A lot of their videos are mindless fun, but it’s always refreshing to see a video where the Lonely Island has something to actually say.

8 3-Way (The Golden Rule)

It's nice to have messages, but sometimes the comedy trio just likes to do something goofy. "3-Way" continues right after the events of previous entry, "Motherlover." After Timberlake and Samberg exit each other's mom's houses, they give themselves a pat on the back and go about their day. Each boasts that they're going to see a different cutie that they met last week. To their surprise they wind up at the same apartment and none other than Lady Gaga answers the door, who says she wants to have a 3-way with the 2 '90s crooners

Timberlake and Samberg proceed to start singing about a minajatwa, and how it isn't weird with 2 dudes, especially when those 2 dudes are best friends. In their eyes, it certainly isn't gay if there's a woman in the middle, which they refer to as "the golden rule." The song gets a little uncomfortable as the trio throws around sex puns that come faster (not an intentional pun) than a James Bond movie, but that uncomfortable feeling never ceases to get a laugh.

7 Boombox

It's no secret that the boys in the Lonely Island are huge fans of '80s culture. Their first feature film, Hot Rod, is a love letter to the commercialized decade where parachute pants, keyboard synths and hair bands ruled the day. Clearly their digital short, "Boombox," is also lovingly nostalgic, conjuring about the sappy images of John Cusack holding his boombox above his head on his girlfriend's front lawn. Here, Samberg employs a similar technique like the one in Say Anything, playing his beloved boombox in the stuffiest of places, with help of The Strokes lead singer Julian Casablancas, no less.

The 2 hipsters suit up in cliché '80s gear, including leather jackets, big sunglasses, and fingerless gloves with Rubik's cube color schemes as they pump the beat everywhere they go. They journey to board room meetings and old folk's homes to inject the masses with a little bit of boombox magic, and before they know it everyone starts uncontrollably starts dancing to the rhythm. It's a sketch that's weird, but in it's obscurity, somehow works.

6 On the Ground

No one is off limits to satirizing when it comes to the Lonely Island, least of all hipsters. In true parodying fashion, Andy Samberg plays a young poser obsessed with non-conforming and refusing the evil ways of the "system." The confused beatnik wanders around his city, mercilessly throwing things on the ground when he either doesn't understand them, or just plain doesn't like them. When he gets a free energy drink shot, he throws it on the ground. When he gets a free hotdog, he throws it on the ground. A piece of a child's birthday cake? Ground.

The highlights of the sketch are undoubtedly the celebrity cameos consisting of Ryan Reynolds and Elijah Wood, who are less than delighted when Samberg's beatnik decides to throw their dinner table to the ground. As a result they chase down the hipster, subdue him, and continue to taser his butthole. The moral of the story? You can't trust the system.

5 I Just Had Sex

In this skit, Jorma and Andy had such a great time having sex, they just had to tell the world about it. And when you're telling the world that you just banged, nothing is more self reassuring than having Akon sing by your side on the chorus. A video notable for its plain silliness, "I Just Had Sex" is an anthem so preposterous and hilarious that it caught on like wildfire when released on their second studio album, Turtleneck & Chain.

The first single off that album, the song went viral after the digital short made its way onto the internet. The video shows Andy and Jorma boasting about their sexual escapades while their girlfriends (played by Jessica Alba and Blake Lively) seem relatively unsatisfied and disgusted. It doesn't phase the boys none, as they continue to shout on rooftops with Akon that they just did the nasty.

Fun fact: You may recognize the top of the building where the group shouts about their sexual conquests, as it was also used as Stark Tower in Marvel's Avengers.

4 Jack Sparrow

This is what happens when you hire Michael Bolton to sing a big sexy hook on your electronic banger about living it up in the club. As Jorma, Akiva and Andy sing about picking up chicks at the local nightclub, in enters Michael Bolton, decked out in full Jack Sparrow gear, singing about Pirates of the Caribbean. Annoyed that their R&B anthem about partying was being turned into a pirates song, the Lonely Islanders employ Bolton to fix his chorus, which he does by also singing about Forrest Gump, Erin Brockovich and Scarface.

Directly after the video was shot, Michael Bolton went on his facebook and made a post describing the shoot as one of the most memorable experiences of his life. Surprising to say the least, as the Grammy award winning singer dresses up like Tony Montana at one point and sniffs mountains of fake cocaine. It just goes to show how alluring being in a Lonely Island video can really be.

3 Lazy Sunday

"Lazy Sunday" is the Digital Short put the Lonely Island on the map and made them a household name for every high school kid at the time. Played on SNL and catapulting the trio into superstardom, this hardcore rap is about nothing other than 2 guys hanging out on a lazy Sunday afternoon. The concept is brilliant, and as it turns out, very appealing. Samberg and fellow SNL cast member Chris Parnell wake up in the late afternoon, grab some cupcakes for a snack, pick up some Mr. Pibb and Red Vines, and then sneak the snacks into their matinee showing for the Chronic (what?) cles of Narnia.

The video short caused a complete viral frenzy. Beforehand, Taccone and Schaffer, both SNL writers, were only able to get 2 of their sketches past the writing phase. But after this video aired, they were the most sought after writers on the program, and were credited with bringing the improv sketch show back into mainstream eyes. Who knew that making a rap video about doing boring stuff on a Sunday afternoon could be so entertaining?

2 D*** in a Box

If "Lazy Sunday" was a breakout success, "D*** in Box" was an all out smash hit. It's hard to think that a song about sticking a penis into a box, and wrapping it up as a gift for your special lady would become an instant classic. But that's exactly what happened that fateful night on SNL, when Justin Timberlake and Andy Samberg dawned  their cheesy '90s R&B personas for the first time, and crooned about laying it all the line.

Legend is that Lorne Michaels, the creator of Saturday Night Live, asked Samberg to write a song that would showcase Timberlake's music skills, who was the host for that particular episode. The Lonely Island crew apparently wrote the song in one night, and then shot the entire thing the next day. When it finally aired on television, it was beeped 16 times for each separate occasion it used a certain word in the title. More shocking than anything, was that it also won a Creative Arts Emmy for Outstanding Music and Lyrics. Keep in mind that the song is titled, "D*** in a Box."

1 I'm On a Boat

If you've ever been on a boat in the summertime, chances are you've sang or have heard one of drunk buddies sing this Lonely Island jam. This is the song that defines everything that the comedy troupe stands for. It pokes fan of hip hop, it has a celebrity singer cameo (T-Pain) and it's surprisingly catchy for being a parody. After winning a boat ride for 3, Samberg snubs his buddy Jorma, and instead brings Akiva and T-Pain on a kick ass ride on a yacht. All the while the 3 state the obvious, that they're on a boat, and they're loving every second of it.

It's an obvious parody of overblown rap videos and the artists in them, who are so very dead set on showcasing their money that they shoot on an expensive yacht whenever they can get the chance. This auto-tuned hit is so simple and catchy, you just can't help but sing along as Samberg and Akiva have a blast on their party boat in tuxedos, while Jorma is left to his lame escapades on dry land.


What are your favorite Lonely Island videos? Let us know in the comments!

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