Make ’Em Laugh

A list of the funniest songs of all time

Fine, so songs are supposed to inspire us, make us dance and provide the background for wedding videos. We get it. Still, once in a blue moon, they manage to simply make us laugh. So, in honor of April Fools’ Day, we present an earful of the funniest tunes of all time.

“Trapped in the Closet,” R. Kelly

Clocking in at an insane 84 minutes, this epic tale of cheating is chock-full of guns, leg cramps, Popeyes chicken and, of course, cherry allergies. The most fascinating part of “Closet” is Kelly’s complete and utter commitment. One gets the feeling that he wants this ditty to speak to his memory for all time. And that makes it all the funnier.

“Dick in a Box,” Justin Timberlake and Andy Samberg

What is it about Saturday Night Live that turns Justin Timberlake into Steve Martin? It seems that his every visit to Rockefeller Center churns out a few classic bits, none more memorable than this viral parody of early ’90s R&B. What could be more generous than presenting your significant other with a box of your own genitalia?

“Yes! We Have No Bananas,” Various Artists

This American classic was first sung in a 1922 Broadway revue by Eddie Cantor, but three different acts recorded and released it within weeks. The song is a Vaudevillian tale, full of vendors attempting to sell people everything other than bananas, never fully admitting to a lack of them. Legend has it that it was inspired by an actual Brooklyn banana shortage.

“Lumberjack Song,” Monty Python

The blokes from Monty Python gifted us many a fine tune, and narrowing it down to one is akin to donating your organs before you’re dead. This little ditty is a classic, starting out as a salute to the lumberjack before spiraling into an ode to cross-dressing, much to the chagrin of the Mounties singing the chorus.

“Rapper’s Delight,” The Sugarhill Gang

This venerable, landmark hip-hop song presents us with an endless volley of meaningless scat and hilariously dated lyrics. The tune builds to an epic verse, when Wonder Mike steps forward and details an awful experience as a dinner guest. Mike’s rhymes take us back to a simpler time, when poorly made macaroni, and the gastrointestinal havoc it wreaks, was enough to win any rap battle.

“James K. Polk,” They Might Be Giants

Few bands are as clever as TMBG. On “Polk” they’re in the zone, covering the reign of one of our most anonymous commanders in chief with one hell of a song. Thank God for TMBG, otherwise we might never have known that Polk forced the British to sell Oregon. “Debra,” Beck

Sung in an unforgettable falsetto, this is Beck’s tale of a low-rent, San Fernando Valley (Calif.) smooth-talker hitting on a JC Penney clerk named Jenny. However, as the song progresses, it’s clear that he is interested in much more than just her. I want to get with you (only you), and your sister, I think her name is Debra. Beck, you naughty, funny man.

“The Bleach Boys,” The Dead Milkmen

Hailing from Philadelphia, the Milkmen somehow managed to successfully navigate the choppy waters of humor-punk. This song is the treatise for a group of suicidal teenagers who, bored with the increasing madness of our world, turn to drinking bleach as a cure-all. Don’t you wanna hang out with The Bleach Boys, baby, in a world where ministers murder golf pros? The Milkmen saw Springer coming a mile away.

“Sunshine, Lollipops and Rainbows,” Lesley Gore

This 1965 gem is so unabashedly happy that it winds up becoming a parody of itself. As if sunshine, lollipops and rainbows (the holy trinity of happy things) weren’t enough, even lucky pennies make an appearance. If only the Bleach Boys could have listened to this song first, they surely would have reconsidered. “A Boy Named Sue,” Johnny Cash

Written by the legendary children’s poet Shel Silverstein, this classic tells of a tough boy with a girl’s name and his showdown with the absentee father who named him. Of course, whooping the old man turns out to be easier said than done. This track was recorded live at San Quentin State Prison (Calif.), undoubtedly played to a room full of guys raring to beat the crap out of their own dads.

So there you have it, a laugh-a-minute iTunes playlist waiting to happen. A special Lifetime Achievement Award goes to “Weird Al” Yankovic. He deserves a mountain of credit for a humor song career that has lasted more than three decades, garnering him three Grammys and several platinum records. Shine on, you weird, weird prince.

Dan Ewen is a comedy writer from Los Angeles who has managed to slowly wear a path between the beach and the Strip.

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