Looking back at the best and worst novelty rap songs

When Biggie Smalls asked “Remember ‘Rappin’ Duke’/Duh-huh, duh-huh,” a whole generation of rap fans had to ask their elders what the hell he was talking about. Shawn Brown’s hip-hop parody found the artist adopting the tougher-than-leather persona of John Wayne to poke fun at other emcees’ boastfulness and, midway through the song, to recount the political rise of Ronald Reagan via the lyrics of “The Beverly Hillbillies” theme song. Though it didn’t burn up the Billboard Hot 100 (rap rarely did prior until Run-DMC/Aerosmith’s crossover smash, “Walk This Way”), it got loads of Top 40 airplay (also unusual for rap songs). One wonders if the song would’ve hit the mainstream to the extent that it did had listeners known Brown was African-American.

There are many football experts who believe the 1985 Chicago Bears were the greatest team in the history of the NFL, and its possible the only blemish on their record, a Monday Night Football road loss to the Miami Dolphins, could be blamed on this collection of bruisers having temporarily lost their focus because they were scheduled to record the most memorable novelty rap of all time the following morning . Aside from literally no-nonsense defensive tackle Dan Hampton, the entire team participated; ten top players (including Walter Payton, Willie Gault, Mike Singletary, Jim McMahon and marketing sensation William “Refrigerator” Perry) rapped lyrics penned by Richard E. Meyer and Melvin Owens, and did a fine enough job in the eyes of the Recording Academy to earn a Grammy nomination for Best R&B Performance (they lost to Prince, thank god). Most importantly, they won the Super Bowl. Otherwise, they’d be remembered as the greatest chumps in the history of the NFL.

The Fat Boys were better personalities than rappers, but this was precisely what the nascent, deeply disreputable genre needed if was ever going to cross over to white America. Inspired by the success of Run-DMC and Aerosmith’s “Walk This Way”, the lovable trio hooked up with Baby Boomer legends The Beach Boys for a cover of an oldie the latter band never performed. No one cared. The song was a Billboard smash, and the awful video (which doubles as promotion for a then-unmade boxing match between Ray Mancini and Hector Camacho) received brutally heavy airplay on MTV. But The Beach Boys’ involvement gave rap a much-needed seal of approval – as did The Fat Boys’ pandering follow-up, “The Twist” featuring Chubby Checker.

Rodney Dangerfield was sixty-two years old when he cut his first rap track, which has to be some kind of record. The actual record was a part of a 1983 comedy LP, which hit in between his big-screen breakthrough (“Caddyshack”) and his first star vehicle (“Back to School). The long-struggling Catskills comic had hit the stand-up big time thanks to Johnny Carson in the 1970s, and this very ‘80s single essentially cherry picks Rodney’s most withering self-putdowns (“I told my doctor I want to stop aging, he gave me a gun”). The song was a Top 40 radio hit, and spawned a heavy-rotation music video costarring Pat Benatar and Father Guido Sarducci.

One of the weirdest novelty hits of the 1980s came from Kip Addotta, a punny stand-up comic familiar to viewers of “The Tonight Show”, “Make Me Laugh” and “Hollywood Squares”. It’s an aquatic-themed parody of a hardboiled detective voiceover in which our narrator’s rental Stingray breaks down (his Barracuda is in the shop), which leads him to grab a drink at a local dive bar owned by a former Dolphins player named Gil (who’s hard of herring). Aside from a joke about blowing a seal (designed to sail over the heads of any kids within earshot), the title is the dirtiest thing about this relentlessly silly (and cornily clever) song.

Though “SNL” belonged to Eddie Murphy in the early 1980s, Joe Piscopo delivered a multitude of yuks as a peppy sportscaster, an infallible Frank Sinatra, and Doug to Robin Duke’s Wendy Whiner. Within that universe, he was a star. But like many other “SNL” standouts, his post-30 Rockefeller career didn’t immediately take off. It certainly didn’t skyrocket like Murphy’s. So to give it a jumpstart, he recorded a comedy LP titled “New Jersey”, the centerpiece of which, “Honeymooners Rap”, found Piscopo and Murphy recycling old bits from the classic sitcom (as, respectively, Jackie Gleason and Art Carney) over a hip-hop beat. That was the hook, which, in 1985, lacked the gut-busting power of Murphy’s own “Honeymooners” routine on his HBO comedy special, “Delirious”. And so it bombed. The best that can be said about “Honeymooners Rap” today is that it can still be played, whereas Murphy’s homophobic "Honeymooners" bit has worn horribly.

Simpsons fever was running high in 1990 when this earworm hit the airwaves at the outset of the show’s second season. Though the song is credited to Michael Jackson collaborator Bryan Loren, Matt Groening later confirmed that Jackson, a huge fan of the show, co-wrote and –produced the track. Voice actor Nancy Cartwright rocks the mic as the character that made her a multimillionaire, and the song bops along with funky insouciance worthy of its subject. This chart-topper cost “The Simpsons” some cool points among its most ardent fans, but the remarkably consistent quality of the writing kept the show relevant for decades and counting.

Following his breakthrough performance in “Coming to America”, and just before his surprise success as a late-night alternative to Johnny Carson, Arsenio Hall cut an entire comedy rap album as Chunky A. Superficially a parody of overweight emcees like The Fat Boys, Heavy D and Biz Markie, “Large and in Charge” takes aim at the genre’s puerile preoccupations (women, wealth, and in a jarringly serious moment, drugs). But despite the involvement of big names Cameo (who help spoof their own hit, “Word Up”, on “Owww!”) Hall’s act never caught on. Alas, with dated tracks like a “She Drives Me Crazy” parody titled “Ho Is Lazy” (featuring lyrics like “You lie around the house so much, I should’ve married a rug”), the sole entry in Chunky A’s oeuvre feels decidedly unripe for rediscovery.

“Weird Al” Yankovic had fallen off the pop cultural radar by the mid-1990s, but he scored his biggest Billboard hit in years with this deeply silly parody of Coolio’s dead-serious “Gangsta’s Paradise”. Yankovic’s best parodies (“Eat It”, “Fat” and “Smells Like Nirvana”) have always gently undercut the artist’s sober intent, and folks like Michael Jackson and Nirvana took the joke well. Coolio, on the other hand, chose to beef with Yankovic, which only gave the comedic genius years of material until the hip-hop flash-in-the-pan realized what an honor it was to be goofed on by the King of Spoof Pop.

James Todd Smith, aka LL Cool J, was all of eighteen years old when he penned the “Football Rap” for Michael Ritchie’s raunchy comedy starring Goldie Hawn as an overwhelmed high school football coach. It didn’t get much radio play, but the end credits reprise featuring verses by the film’s young actors is something of a cult favorite. After all, what’s not to love about watching soon-to-be stars like Wesley Snipes, Woody Harrelson and Mykelti Williamson pass the mic while Hawn struggles to chime in with “Football” on time? (Harrelson is a surprisingly deft emcee, exiting his verse with the casual ease of Biggie Smalls on “Party and Bulls**t”).

Robert Smigel is one of the greatest comedy writers of the last half-century, and yet he’s probably best known to the public as the man whose hand manipulates a cigar-chomping, insult-slinging Rottweiler named Triumph. The act’s popularity prompted Smigel to cut a comedy LP called “Come Poop with Me”, the highlight of which, “I Keed”, doubles as a showcase for Triumph’s acerbic barbs and a meta parody of moldy novelty tracks like the aforementioned “Rappin’ Rodney”. The insults are very 2003 (Britney Spears, Justin Timberlake and Fred Durst are its juiciest targets), but it’s still hilarious seventeen years later.

When the “Rock ‘n’ Wrestling” phenomenon launched the World Wrestling Federation into the “sports entertainment” stratosphere, Vince McMahon greenlit “The Wrestling Album”, an assortment of tracks spotlighting the league’s most beloved grapplers, none of whom could sing. The second Wrestling Album, “Piledriver”, got with the times and incorporated a rap track from up-and-coming manager Slick. "Jive Soul Bro" is basically a cleaned-up, Dolemite-style saga of failed sexual conquest, the intent of which is to make Slick look like a clown. The 1988 video, and, let’s face it, Slick’s persona are highly problematic.

You know Kurtis Blow’s “Basketball”, but have you ever heard Hurt ‘Em Bad’s “NBA Rap” ? Recorded two years prior to Blow’s hardwood classic, DJ George Luster’s track is a basketball nerd’s dream – provided that basketball nerd grew up in the late ‘70s and early ‘80s. Luster fantasizes about shooting like “Pistol” Pete Maravich and scoring on David Thompson, Jack Sikma and Artis Gilmore, but he does make time for (then) newcomers like Magic Johnson. It’s fairly perfunctory lyrically (“I’d set the picks, make the screens/I’d be the captain of the team”), but that’s part of its charm. There’s no reason this song shouldn’t be updated every four years.

The Timex Social Club made one-hit-wonder history with their sing-songy hip-hop track, “Rumors”, so it feels appropriate they’d spawn a one-hit-parody-wonder in the form of “Roaches” from Bobby Jimmy and the Critters. Instead of people spreading salacious stories, Bobby Jimmy is concerned with a cockroach infestation in his house. Here’s a representatively silly verse: “Lots of pesticides/Big money I done spent/None of them be workin’/So I charge my roaches rent.” Bobby Jimmy puts it over with a goofy voice that sounds a bit like John Witherspoon.

“A Nightmare on Elm Street 3: Dream Warriors” got a sweet PR bump from its hard-rockin’ Dokken theme song in 1987, but the series’ producers opted for a hip-hop track to promote “A Nightmare on Elm Street 4: The Dream Master”. The Fat Boys had fully crossed over to the mainstream thanks to “Wipeout” and “The Twist”, so they were the safest bet in town. “Are You Ready for Freddy” is forgettable fluff, notable solely for Robert Englund getting to spit a few clunky rhymes as child murderer Freddy Krueger. The music video reveals Prince Markie Dee is distantly related to the blade-fingered monster, so that makes The Fat Boys a canonical part of the “Nightmare” franchise.

Fred Dekker and Shane Black’s immensely entertaining yarn about a bunch of precocious kids who take on the classic monsters (Dracula, The Mummy, The Wolf Man and The Gill Man) bombed at the box office, which is probably why the tie-in rap went absolutely nowhere. It’s credited to “The Monster Squad”, but it’s performed by a professional emcee, not the actors. Music industry veterans Michael Sembello (“Maniac”) and Richard Rudolph (Minnie Riperton’s collaborator, husband and, yes, father to Maya) wrote and produced the track, so it sounds better than most movie tie-ins of that era. But who’s the mystery rapper?

In the utterly wretched “Weekend at Bernie’s II”, the still-deceased title character (Terry Kiser) gets partially reanimated by a voodoo priest in the Virgin Islands. This causes him to lurch about like a spastic zombie, which isn’t at all funny in the movie, but became inexplicably hilarious two decades later when hip-hop artist Isa turned Kiser’s movements into a dance craze. “Movin’ Like Bernie” was not quite the Dougie or the Nae Nae, but it did catch on with some athletes and briefly became a viral sensation.

If you’ve kept up with Netflix’s excellent “GLOW”, you know that scrappy, all-female Gorgeous Ladies of Wrestling left no fad unexploited while promoting their upstart league. Their most memorable marketing ploy was an opening credits rap song wherein the ladies introduced themselves. The rap was used as an advertisement (incessantly), so if you watched a lot of late night television in the ‘80s, you can probably still recite this from memory.

Everyone! “They do what they wanna do, say what they wanna say/Live how they wanna live, play how they wanna play/Dance how they wanna dance/Kick and they slap a friend/The Addams Family!” Having the chorus memorized due to heavy MTV rotation is one thing; if you’re a true “Addams Groove” connoisseur, you can still do the accompanying MC Hammer choreography. Hammer was still on top of the pop-rap world when this tie-in single dropped, so no one could’ve predicted that this would’ve been the very last Billboard top ten hit of his career.

The rapidly broadening hip-hop culture was ripe for parody in 1993, and who better to deliver an affectionate elbow to the ribs than Chris Rock? The film’s fictional group is largely based on NWA, which leads to a direct parody early in the film called “Straight Outta Locash”. It’s an absurd goof on NWA’s signature song padded out with lots of momma jokes. Rock, as MC Gusto, threatens to have sex with a house cat at one point. CB4’s other big hit, “Sweat of My B****s”, offers more of the puerile same.

Chris Rock got to theaters first with “CB4”, but Rusty Cundieff’s hip-hop parody is generally considered to be the superior work. While Rock and company only wrote a few full songs for their soundtrack, Cundieff released an entire soundtrack’s worth of cuts. There are several standouts (e.g. “Booty Juice”, “Granny Said Kick Yo A**” and “Ice Froggy Frog”), but the best of the bunch has to be this parody of NWA’s most notorious single.

The fickle, fast-churning culture of hip-hop had turned rap legends Run-DMC into seeming has-beens by 1989. The failure of their blacksploitation throwback, “Tougher Than Leather”, certainly didn’t help, but nothing did more to tarnish their reputation than their rap reworking of Ray Parker Jr.’s hit theme song for the first “Ghostbusters”. Alas, the track was every bit as uninspired as the sequel (though you do get to see Sigourney Weaver and Annie Potts sporting hip-hop bling in the video). After several failed comeback attempts, the trio bounced back in 1993 with the Pete Rock-produced “Down with the King”.

Joeski Love’s one-hit classic had no official association with “Pee Wee’s Big Adventure”. In fact, Joeski hadn’t even seen the movie when he a music producer asked him to write it. Working from a friend’s recollection of the movie, Joeski dashed off some lyrics, “borrowed” a beat from an Audio Two demo tape (with a keyboard riff on the “Tequila” melody) and suddenly had an underground hip-hop smash. The video sports a cameo from Mark “Francis” Holton as a science teacher, and features clips from the movie, but, alas, Paul Reubens is a no-show.

Tom Hanks was six years away from winning his first Best Actor Oscar when he plopped down in a recording studio with his Jack Webb-impersonating costar Dan Aykroyd to record this tie-in rap classic. What's more, they shot a one-off music video (with choreography by Paula Abdul) that played ceaselessly throughout the summer of 1987, and was promptly forgotten. Recently, on the "Conan O'Brien Needs a Friend" podcast, Hanks revealed that his introduction to YouTube many, many years ago was when his son played the video on his laptop at the dinner table. He'll never escape this. (Nor should he, because it's still kinda funny!)

Vanilla Ice’s performance of “Ninja Rap” in the execrable “Teenage Mutant Ninja Turtles II: The Secret of the Ooze” provides viewers with the rare opportunity to watch a celebrity’s fifteen minutes expire in real time on camera. The actual music video is somehow even more embarrassing (dear god, that opening). There was no coming back from this, as evidenced by Universal Pictures’ unceremonious dumping of Vanilla’s first-and-only star vehicle, “Cool as Ice”, later that fall.