Incredibad

By the time Incredibad came out in February 2009, comedy troupe The Lonely Island (Andy Samberg, Jorma Taccone, Akiva Schaffer) were already famous: Their digital shorts on Saturday Night Live (“Lazy Sunday,” “D**k in a Box,” “I’m On a Boat,” “Like a Boss”) were among the first viral videos to be given the name and set standards for the bridging of old and new media—a template that feels familiar now but in 2005 was unprecedented.

In that sense, Incredibad could’ve easily been an afterthought or easy cash-in. Instead, it was arguably the definitive piece of musical comedy of its time, an album that didn’t just mock its source material but emulated it, delivering full-blooded send-ups of hip-hop that actually felt like hip-hop. That they collaborated with real musicians—Justin Timberlake, T-Pain, Norah Jones, E-40—didn’t hurt either, nor did the fact that they showed genuine deference toward the art of rapping. Here were three mild-mannered college-town white boys approaching rap not from a place of condescension or entitlement, but love. Put another way, Incredibad wasn’t just parody—it was tribute.

Part of the album’s grace was that the humor aimed beyond music. It’s hard to think of a more elegant lampoon of rap materialism than “I’m On a Boat” (“Take a good hard look at the motherf**king boat!”), or a slow jam clumsier than “D**k in a Box” (“Gonna give you something so you know what’s on my mind,” crooned over fake fireplace crackles). But more often than not, the group’s jokes were on themselves: how they’re awkward (“We Like Sportz”), nerdy (“Lazy Sunday”), fake (“Ras Trent”), or, in a subject they got considerably more mileage out of as time went on, really bad at sex (“J**z in My Pants”). As for the Natalie Portman-featuring “Natalie’s Rap”: Yes, the joke lies in the dissonance of hearing someone as wholesome as Natalie Portman rap about defecating on your face, but one, it’s based on an Eazy-E track, and two, it’s hard. “We want to be the greatest fake MCs on earth!” they rapped on the title track—a wish issued to an alien in exchange for sex. (It’s a long story.) When you put it that way, they’d won before the game even started.