It’s one thing to lean on something uncharacteristic for comedy. It plays against type, serves as a shock to the viewer, and often offers an amusing juxtaposition. Unless of course, you’re having a white actor bust into a rap for the sake of all the 37 year-old receptionists that will reflexively squawk, “I can’t believe they went there!” That's not funny. That's not even humor. Nonetheless, films and TV have long been in the business of "surprising" audiences with familiar stuff they've seen before, and this “rapping cracker” business has become old hat.

Here are a few of the most glaring instances. A few work on a deeper level, but most don’t. If any of these scenes are personal favorites of yours, I’m sorry. Sorry you have bad taste.

Ok. The 30 Rock one is pretty damn funny.

Chris Cooper – The Muppets

Sadly, no video is available for this one yet, but Chris Cooper, who plays a humorless oilman in the puppet film, breaks into a rap entitled “Let’s Talk About Me.” There are video vixens, crazy-phresh lyrics, and, most importantly…CHRIS COOPER RAPPING. While it’s certainly an irreverent scene by Muppet standards, the oddness of it all works. It’s weird, but not in a desperate or incomprehensible fashion. It’s just pretty interesting.

I thought about tagging this with a “spoiler alert,” but figured those diehard Muppet fans that would get upset by this have all seen the movie by now. If that’s not the case, I’m sorry I ruined his ironic rap.

Ellen Dow – The Wedding Singer

Hey! The rapping Granny is rapping! And she’s old. In a film that is inundated with thoughtful humor and cheap gags, this certainly falls in the latter camp. Dow was 80 at the time The Wedding Singer was released, and I still have doubts as to whether that’s her natural voice. My theory? She couldn’t rap that fast, so they sped up the tape, raising the pitch.

You can read the complete theory in my upcoming book, The Agony and the Anguish: How ‘The Wedding Singer’s Rappin’ Granny Came To Be.

Mike Meyers – Austin Powers: The Spy Who Shagged Me

Again, another cheap gag in a movie that’s filmed with them, this rap scene between Dr. Evil and Mini-Me works because at this point in the film (and the franchise), the presence of Verne Troyer running around onscreen is still pretty funny no matter what the context. This rap scene is a nod to Will Smith’s remake of Grover Washington’s original, only Smith’s version focused on the love between a father and son, rather than a couple. Austin Powers took this one step further by suggesting that perhaps the song focuses on the love between a man and his one-eighth-sized clone. Because that’s the greatest love of all.

David Schwimmer/Jennifer Aniston – Friends

Stuff white people like: Friends, “Baby Got Back,” and ironic rap songs shoehorned into their entertainment.

In a convoluted set up to get Ross and Rachel to sing the song, Ross discovers that the only way he can get his daughter Emma to laugh is to sing the early-90’s booty anthem to her. Rachel is upset at the inappropriateness of this song (white people are so uptight!), until she is also forced to rely on it to make her daughter laugh.

There is an upside to this hackneyed storyline. Sir-Mix-A=Lot, nee Anthony Ray, got not one, but two royalty checks from his song appearing in the sitcom. I wish the writers had just made the whole episode a series of the friends continuously rapping Baby Got Back. The episode would be called “The One Where Sir-Mix-A-Lot Gets Fuckin’ PAID.”

Tina Fey/Scott Adsit (Featuring Jack McBrayer) – 30 Rock

30 Rock’s use of Rob Base and DJ EZ Rock’s “It Takes Two,” is a little different. It’s not shoehorned in for the nostalgia value (though that’s a happy coincidence), but rather to put a spotlight on Kenneth Parcell singing the hook with gusto. Sure, it’s yet another example of having a white guy singing a rap song ironically, but referring to Kenneth Parcell as “a white guy” is a bit like referring to Kim Jong-Il as “an Asian guy;” it fails to take into account the “crazy” factor.

Warren Beatty – Bulworth

There will always going be traces of irony in any rap performances by white guys whose names don’t rhyme with “treminem,” but the Bulworth raps, which are the fundamental concept of the film, are the least ironic on this list. This is a guy who is so repulsed by everything he has stood for as a white politician that he swings the pendulum the other way, representing the ideas of a marginalized class.

Sure, it’s ironic, but it’s irony with a purpose, rather than irony for the sake of “I can’t believe that white guy went there!”

Justin Timberlake – Friends with Benefits

This scene is a dangerous union of irony, nostalgia, and Justin Timberlake’s dreamboat charm. I feel queasy. If Justin Timberlake can’t even pull off a musical number without it feeling completely contrived, then its utilization represents perhaps too heavy of a hand. He should avoid this low-hanging fruit (which the film had in spades) and go back to singing about how much Britney Spears sucks.

Let's ALL put out albums about how Britney Spears let us down. Mine is gonna be called Sob Me A Creek.

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