13 of the Funniest Jokes, Songs and Bits from The Lonely Island

At Willard Junior High School in the early 1990s, Andy Samberg, Akiva Schaffer and Jorma Taccone formed a comedy troupe that would create some of the funniest music videos and sketches of the internet era. Calling themselves “The Lonely Island,” the group became a household name, ushering in digital shorts to Saturday Night Live and helping YouTube become a pop-culture staple. By the time they left the SNL, the trio had firmly established themselves as one of the leading voices of millennial comedy.

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So let’s dive into the deep pool of funny sketches, songs and bits that made the Lonely Island the comedy icons they are today…

13 ‘Jizz in My Pants’

The Lonely Island rap about a very gross yet relatable problem for some men… IT’S A SENSITIVITY ISSUE!

12 Natalie Raps

On Saturday Night Live, the boys got guest host Natalie Portman to flex by dropping bars about her day-to-day life and schedule.

11 Cool Guys Don’t Look at Explosions

In which they point out the badassness of a popular action movie trope — walking away calmly from a giant fiery explosion.

10 ‘Doubt: The Video Game’

Give us more Meryl Streep games.

9 ‘I Just Had Sex’

Akon helps The Lonely Island thoroughly explain how great sex feels (for men, at least).

8 Punched Right Before Eating

It’s everyone’s favorite violent, celebrity-laden prank show! Just watch out for zombies.

7 ‘Diaper Money’

These grown-ass men attack responsibility HARD.

6 ‘Lazy Sunday’

The hit that cemented their status on Saturday Night Live, “Lazy Sunday” showcases what the group is known for: sick beats and rhymes wrapped up in general silliness.

5 ‘Like A Boss’

A performance review doesn’t go as hard as this song. Definitely deserving of a promotion.

4 ‘Threw It On the Ground’

There’s no better song of misplaced rebellion than this anthem against “the system,” which is just a bunch of people being nice and considerate. I’M AN ADULT.

3 The Shooting (Dear Sister)

The sketch may be a little dated since it references The O.C., but the gag itself is timeless.

2 ‘Dick in a Box’

In arguably their best digital short, Lonely Island teamed with Justin Timberlake to present a new crude holiday love song for a generation raised on ’90s R&B.