Ask random people for their favorite year in music, and they'll often name the year they turned 19. Ask people under 50 for their favorite "Weird Al" Yankovic record, though, and they're likely to come up with the one that came out when they were 12 or 13. That idea helps account for Yankovic's many comebacks: New 12-year-olds are minted every day, and as listeners age into adulthood, they're not likely to leave behind the man who helped provide their gateway into grown-up comedy – and in the process made adolescence a tiny bit bearable.
But that alone doesn't account for Yankovic's incredible staying power. He's also evolved constantly as he's moved from spare early parody singles (1979's "My Bologna," 1981's "Another One Rides the Bus") to the masterfully joke-dense satires and lavishly arranged originals that fill his later records.
Yankovic's self-titled debut album came out exactly 40 years ago on May 3, so I decided to mark the occasion by doing the only reasonable thing a person who's been a fan for that entire span could possibly do: I listened to all of his songs in chronological order and ranked the 40 best. The man has assembled a remarkably diverse catalog, too: There are song parodies, of course, but also originals, pastiches (Yankovic calls them "style parodies"), polka medleys, TV theme songs and even movie skits to choose from.
Now, a rigorous adherence to professional ethics dictates that I acknowledge a personal bias, in the form of my fondness for the man himself. I idolized him as an adolescent dork in the '80s, I've known him since the late '90s, he contributed commentaries to a book I edited in 2002, I wrote the liner notes to his 2009 compilation The Essential "Weird Al" Yankovic, I produced his Tiny Desk concert in 2010 and I even got to play a tiny role in his effort to secure Lady Gaga's permission to parody "Born This Way" in 2011.
With that caveat out of the way, I tried not to ding songs too hard for aging poorly, whether due to out-of-date cultural references or phrasing and terminology that wouldn't fly today. (Any comedy catalog spanning 40 years is bound to contain a few punchlines that have curdled into slurs, and Yankovic's is no different.) And I decided early on to pick at least one song from every full-length studio album, just to capture the breadth of work here. That approach was easy when the album at hand was, say, Straight Outta Lynwood or Alpocalypse, but it took a little more digging when it came to Polka Party! or the consistently good-but-not-great Alapalooza.
40. "Christmas at Ground Zero," Polka Party! (1986)
(Original)
Polka Party! was Yankovic's fourth album, after a string of records that rank among his classics. When it tanked, peaking on the Billboard albums chart at No. 177, it seemed like a career-ender: the last hurrah of a novelty act that had run its course. Listening back, it mostly just sounds uninspired, particularly when it comes to one-dimensional parodies like "Living With a Hernia" and "Addicted to Spuds." Still, the album closes with a Yankovic original that might have aged into a holiday classic, had the phrase "Ground Zero" not assumed greater significance in the fall of 2001. In its time, though, "Christmas at Ground Zero" recalled the dark-hearted cheer of Tom Lehrer, as Yankovic sang of decking the halls and trimming the tree in the immediate aftermath of nuclear annihilation.
39. "Frank's 2000" TV," Alapalooza (1993)
(PARODY: R.E.M.)
Alapalooza is a tricky album to revisit 30 years later. In some ways, it's very much a product of the early '90s: "Bedrock Anthem" sets the story of the Flintstones (who were about to get their own movie) to the tune of the Red Hot Chili Peppers' "Under the Bridge" and "Give It Away," and "Jurassic Park" reworks Richard Harris' infamous 1968 hit "MacArthur Park" to be about rampaging dinosaurs. But it doesn't feel fully plugged into the musical revolutions that were underway – particularly in hip-hop – and leans into the safety of older references. Still, "Frank's 2000" TV" is a timeless, wide-eyed charmer about the envy of the neighborhood and the eighth wonder of the world, rolled into one. Performed in a style reminiscent of R.E.M., it's a harmony-rich earworm.
38. "CNR," Alpocalypse (2011)
(Parody: The White Stripes)
By the time this song came out, its namesake ('70s game-show fixture Charles Nelson Reilly) was decades removed from his heyday. In fact, he died in 2007, before "CNR" first surfaced on Yankovic's Internet Leaks EP in 2009. Still, the song transcends its silly concept — it's essentially taking Chuck Norris Facts and applying them to an un-Norris-like public figure — thanks to funny gags, a nifty video and a rousing rock arrangement that pays homage to The White Stripes.
37. "You Don't Love Me Anymore," Off the Deep End (1992)
(Original)
The mournful closer from Yankovic's early-'90s comeback album is built around understatements that don't stop with the plaintive acoustic arrangement. (Sample acknowledgement: "I guess I lost a little bit of my self-esteem / That time that you made it with the whole hockey team.") From there, "You Don't Love Me Anymore" is all severed brakes, piranhas in the bathtub and cobras in dresser drawers — enough carnage to give our narrator the nagging suspicion that all might not be well.
36. "Melanie," Even Worse (1988)
(Original)
Dysfunctional relationships reside at the center of a lot of "Weird Al" Yankovic songs, which makes a certain amount of sense. After all, anyone who spends 40 years parodying love songs is bound to come up with some twisted counterpoints. Still, even by those standards, "Melanie" gets pretty dark — dark enough to trigger content warnings about stalking and suicide — yet it's somehow slight enough to contain one of the most deceptively buoyant choruses of Yankovic's career. At the risk of giving too much away, poor Melanie needn't worry about our narrator by song's end.
35. "Albuquerque," Running With Scissors (1999)
(Original)
Yankovic has said of "Albuquerque" that he'd expected it to be a song even fans would never listen to more than once. "I made it, on purpose, as long and as obnoxious as I possibly could," he told GQ late last year. "I was basically trolling my fans." Naturally, they embraced the song wholeheartedly — all 11 long and obnoxious minutes of it. With a lyric sheet that clocks in at more than 1,800 words, "Albuquerque" unleashes an absolute hailstorm of non sequiturs, asides and explosions of hyperactive id, with a chorus that somehow transforms one word into an earworm.
34. "Gump," Bad Hair Day (1996)
(Parody: The Presidents of the United States of America's "Lump")
One of Yankovic's sturdiest formulas has him using a pop hit as a framework to creatively recap the plot of a hit movie or TV show with the occasional gag tossed in. With its copious references to the 1994 smash Forrest Gump, "Gump" isn't the very best of those songs, but it's the best that isn't in some way connected to Star Wars. It helps that The Presidents of the United States of America's 1995 hit "Lump" kinda plays out like a "Weird Al" Yankovic song to begin with — and that its brief run time keeps the joke from going stale. It also helps that Yankovic opted to spoof Forrest Gump and not a New York real-estate mogul with a one-syllable last name everyone knew in the '90s.
33. "Mr. Frump in the Iron Lung," "Weird Al" Yankovic (1983)
(Original)
Really? A tasteless, two-minute, 40-year-old deep cut makes a list of Weird Al's all-time greatest songs? Trust me: If it hadn't, I'd be on the receiving end of a haughty, handwritten-in-cursive letter from my 12-year-old self. Maybe it's all those memories of "Mr. Frump in the Iron Lung" spinning (and occasionally skipping) on the turntable in a certain pre-adolescent bedroom in tiny, lonely Iola, Wis. Maybe it's the fact that, all these decades later, I could wake up from a dead sleep and still recite every tiny vocal inflection from memory. But let's go with this: "It made me happy when I was 12" is not only high praise, but also cause for deep and abiding gratitude.
32. "If That Isn't Love," Alpocalypse (2011)
(Parody: Hanson)
If you didn't know that "Weird Al" Yankovic is tight with the members of Hanson, you will after hearing "If That Isn't Love," which uses the band's sound as a blueprint nearly 15 years after "MMMBop." The wholesomely Hansonian arrangement provides a perfect canvas on which to paint a portrait of a relationship that only clears the lowest of bars: "Every time I see you trying to lift some really heavy thing," he promises, "you can always count on me to help by saying something encouraging." It's not the most messed-up messed-up-relationship song in Yankovic's arsenal, but it's a sparkling portrait of a romance marked by comically low expectations.
31. "Your Horoscope for Today," Running With Scissors (1999)
(Original)
A curious and oft-hilarious pop-cultural artifact, "Your Horoscope for Today" uses the late-'90s ska revival as the musical backdrop for a series of mock astrological predictions. Heavily inspired by the horoscopes in The Onion (hat-tip to my brilliant friend and former colleague, John Krewson, who wrote most of them in those days), the track lets its arrangement's frenetic pace dictate the sheer volume of gags. "Your Horoscope for Today" is an object lesson in joke density, as well as a reflection of the way Yankovic's songwriting evolved in the early internet era: Throwing a ton of one-liners at the wall means many are bound to stick.
30. "The Weird Al Show Theme," Running With Scissors (1999)
(Original)
In the fall of 1997, Yankovic got his own CBS Saturday-morning TV program, The Weird Al Show. It was canceled almost immediately, but it still has a cult following and it still streams on Peacock, where you can soak up all 13 frenetically silly episodes, complete with guest appearances from the world of comedy, music, TV and movies. (Imagine a playroom big enough to fit Alex Trebek, Dick Clark, Patton Oswalt, Hanson, Teri Garr, Dick Van Patten, Emo Philips, Gilbert Gottfried, Fabio and "Macho Man" Randy Savage, and you've got a pretty good idea.) As for the theme song, it's an appropriately overstuffed 74-second joy — a perfect summation of the chaos the show could barely contain.
29. "Craigslist," Alpocalypse (2011)
(Parody: The Doors)
Digging through 40 years' worth of Weird Al songs is a great way to relive carbon-dated moments in history: fads and phenomena and specific points when some new entity entered our lives and changed the way we go about our business. Craigslist still exists, of course, but "Craigslist" captures with spot-on specificity the way countless listings were (and are) written. Whether or not you've ever made a lowball offer, followed up on a fleeting missed connection, tried to pass off your free garbage as a generous giveaway or written a snotty open letter to a local business, you'll recognize the universal truths behind these vignettes — all delivered with the slithery portentousness of Jim Morrison.
28. "eBay," Poodle Hat (2003)
(Parody: The Backstreet Boys' "I Want It That Way")
While we're on the subject of early internet obsessions, here's a pretty clear sense of what 2003 felt like, minus the wars and whatnot. Sure, The Backstreet Boys' indelible "I Want It That Way" was already four years old by the time Poodle Hat came out, but it's not as if that song has ever really gone away — and, boy, were we ever on eBay. Never let it be said that Yankovic doesn't do the research: This one's got lists of funny possible eBay purchases (ex: "a Kleenex used by Dr. Dre"), critiques of eBay to keep the song from sounding like a commercial and a pitch-perfect feel for the site's intricacies, from "A++" reviews to the folks who wait around and post the high bid with two seconds left on the clock.
27. "Confessions Part III," Straight Outta Lynwood (2006)
(Parody: Usher's "Confessions Part II")
From the moment "Confessions Part II" dropped in 2004, this parody was inevitable; it would have been malpractice for Yankovic not to keep the series going. From the gross-but-mundane ("I haven't changed my underwear in 27 days") to the gross-but-less-mundane ("FYI, it was not a cold sore"), the horrors keep unspooling — not escalating so much as accumulating until it's time, inevitably, to set up Part IV.
26. "Like a Surgeon," Dare To Be Stupid (1985)
(Parody: Madonna's "Like A Virgin")
Yankovic has a policy of not listening to pitches for parodies, but when it's 1985 and Madonna thinks you should writhe around on the floor in medical scrubs, you writhe around on the floor in medical scrubs. The pun at the center of Weird Al's "Like a Virgin" parody doesn't seem on paper like it would yield huge laughs. So call the result a testament to his execution, whether it's the tease in the first verse about how "I still make a mistake or two," the plan to "pull his insides out and see what he ate" or the very idea that Yankovic is "the disgrace of the AMA / 'cause my patients die ... before they can pay." Just solid gags all the way down, and the video's a classic.
25. "I Love Rocky Road," "Weird Al" Yankovic (1983)
(Parody: Joan Jett & The Blackhearts' "I Love Rock 'n' Roll")
Beginning with "My Bologna" all the way back in 1979, food-related tomfoolery has been one of Yankovic's signature moves: He's turned "Girls Just Want to Have Fun" into "Girls Just Want to Have Lunch," "Rico Suave" into "Taco Grande," "La Bamba" into "Lasagna" and so on. The concept of "I Love Rocky Road" isn't any more complex than the others — our protagonist sure does love this particular flavor of ice cream! — but it's a silly and deeply committed goof, performed with utter conviction. "I Love Rocky Road" helped serve notice that Yankovic's band wasn't just backing him up, but also contributing to the comedy by mirroring the energy and sound of their source material.
24. "The Biggest Ball of Twine in Minnesota," UHF: Original Motion Picture Soundtrack and Other Stuff (1989)
(Original)
When my girlfriend ghosted me on my 17th birthday — hang on, I'm going somewhere with this — I went where any young, pockmarked nerd would drown his sorrows on August 1, 1989. I sat in a near-empty theater to watch UHF, Yankovic's debut as a feature-film leading man. The film flopped at the box office (my contribution notwithstanding) but has since found a sizable cult audience, and its soundtrack's highlight remains "The Biggest Ball of Twine in Minnesota," a charming ramble about a family road trip to the Upper Midwest's greatest string-based roadside attraction. More than three decades later, the song remains one of the purest distillations of Road Trip Dad vibes the world has ever known.
23. "Canadian Idiot," Straight Outta Lynwood (2006)
(Parody: Green Day's "American Idiot")
22. "Party in the CIA," Alpocalypse (2011)
(Parody: Miley Cyrus' "Party in the U.S.A.")
It's hard not to combine these two song parodies, given that they represent an identical phenomenon: Their concept and intention are instantly identifiable from their titles, yet they're somehow executed to perfection. In both cases, the source material – by Green Day and Miley Cyrus, respectively – is remarkably sturdy, allowing for extremely high joke density (in the case of "Canadian Idiot") and a funny juxtaposition between the sunny arrangement and lines about torture and assassination (in the case of "Party in the CIA"). Both have a sharp way of exceeding audience expectations without subverting or copping out on the jokes the titles imply.
21. "The Check's in the Mail," "Weird Al" Yankovic (1983)
(Original)
By the time his first album came out, Yankovic had dealt with enough show-business phonies to inspire one of his first (and best) original songs. Fueled by an irresistible sing-song hook, "The Check's in the Mail" unleashes a torrent of funny, smarmily charming, weapons-grade insincerity. It's hard to believe May 3 marks 40 years of "The Check's in the Mail" getting stuck in the heads of Weird Al fans every time they have to make a payment the old-fashioned way.
20. "Couch Potato," Poodle Hat (2003)
(Parody: Eminem's "Lose Yourself")
Poodle Hat is one of Weird Al's three poorest-selling albums — the others are the cursed Polka Party! and the UHF soundtrack, both from the late '80s — but it's not for a lack of great highlights. This TV-centric parody of Eminem's "Lose Yourself" could have easily taken off as the first single, had the rapper not denied Yankovic permission to make a video. It's one of Weird Al's very best songs about TV (one ill-considered Richard Simmons joke aside), as well as an evocative snapshot of virtually every show that aired 20 years ago.
19. "Whatever You Like" (2008)
(Parody: T.I.'s "Whatever You Like")
T.I.'s "Whatever You Like" was a massive hit in the fall of 2008, and Weird Al greeted the song as an opportunity to try a new distribution method. After a speedy permissions process, he released his version — in which the lavish spending documented in the original gives way to Top Ramen, 2-ply toilet paper and a night spent clipping coupons — as a download while T.I.'s song was still atop the Billboard singles chart. (Yankovic's "Whatever You Like" later appeared on the Internet Leaks EP and finally on Alpocalypse in 2011.) It's the only Weird Al song to bear the same title as the work it parodies, but what really jumps out here is the strength of the jokes. "My wallet's fat and full of ones / It's all about the Washingtons" is an A-plus gag, now and forever.
18. "It's All About the Pentiums," Running With Scissors (1999)
(Parody: Puff Daddy's "It's All About the Benjamins [Rock Remix]")
Yankovic's history with hip-hop dates all the way back to a brief Beastie Boys parody on 1988's Even Worse, and the genre has spawned several of his biggest (and best) hits. "It's All About the Pentiums," which parodies the rock remix of Puff Daddy's "It's All About the Benjamins," is especially rousing; when Lin-Manuel Miranda gushed about it in an interview, it marked one of the least surprising endorsements in music history. Are the rapid-fire references to turn-of-the-century computing technology hilariously dated? Sure, but hilarity is kinda the point.
17. "Don't Download This Song," Straight Outta Lynwood (2006)
(Original)
It takes all of two seconds for "Don't Download This Song" to register as a pitch-perfect parody of treacly '80s benefit singles. As with "It's All About the Pentiums," the references are dated — Grokster! Limewire! Kazaa! — but the jokes land from every direction, whether you're Metallica's Lars Ulrich or a 7-year-old girl. There's just one missed opportunity here: Given the sheer size of Yankovic's contacts list, how did he pass up the opportunity to recruit a cast of all-stars for vocal assistance?
16. "The Saga Begins," Running With Scissors (1999)
(Parody of Don McLean's "American Pie")
Yankovic has learned over the years that you don't want to wait too long to get your parody out into the world (see "Whatever You Like" at No. 19, above). So he smartly pulled out all the stops to prepare a song to coincide with the summer of Star Wars: Episode I — The Phantom Menace. He scoured internet spoilers, released "The Saga Begins" while the film was still in theaters and ultimately came up with a song that thoroughly outshined the work it summarized. (You may or may not prefer "The Saga Begins" to Don McLean's "American Pie," but most should agree that it's way better than Phantom Menace.)
15. "Perform This Way," Alpocalypse (2011)
(Parody: Lady Gaga's "Born This Way")
A song parody that doubles as an artist parody, this captures the moment in history when Lady Gaga was emerging from giant eggs and wearing meat dresses instead of crooning with Tony Bennett and dressing down at the Oscars. The sheer pace of Gaga's "Born This Way" necessitated a barrage of jokes about bizarre attire and other efforts to grab attention, as well as a bonus dig at the song's similarities to Madonna's "Express Yourself." But Yankovic nails every one of them — and all while donating the song's proceeds to the Human Rights Campaign.
14. "Polkas on 45," In 3-D (1984)
(Parody: Medley)
All but two of Yankovic's albums come equipped with a medley of hits, performed as polkas with original lyrics intact. And, just in case you've never tried it, listening to them all in chronological order will give you a fascinating snapshot of popular music through the decades. Picking which one to include in this ranking was tough — the format works especially well alongside the self-seriousness of alternative rock and nü-metal, for example — but it made sense to settle on the medley that started it all. For one, it had the entirety of pre-1984 pop and rock music to choose from, which means you get the likes of the Beatles, Jimi Hendrix and The Who jockeying for time with The Lawrence Welk Show's theme song. Bonus points are also awarded for being both a medley and a parody; "Polkas on 45" spoofs the popular-at-the-time early-'80s pop medleys by the Dutch group Stars on 45.
13. "Another One Rides the Bus," "Weird Al" Yankovic (1983)
(Parody: Queen's "Another One Bites the Dust")
This one is crucial to the history of Weird Al — and, by extension, pop music itself. Yankovic's performance of the song on The Dr. Demento Show not only went a very "December 1980" version of viral — it burned up Dr. Demento's request lines for weeks and helped Weird Al land a record deal — but it was also captured mere hours after Yankovic met and began working with drummer Jon "Bermuda" Schwartz. (More than four decades later, Schwartz remains Yankovic's drummer.) The song is genuinely remarkable: It's a memorable Queen parody, sure, but it also features one of the most committed, unhinged vocals of Yankovic's career. "Another One Rides the Bus" actually kicks ass, is what I'm saying. Just try not to recite it like a mantra the next time you're stuck on crowded public transportation.
12. "Pancreas," Straight Outta Lynwood (2006)
(Parody: Brian Wilson of The Beach Boys)
The No. 1 rule of parody is that you have to be able to perfectly duplicate your subject. Just as The Onion wouldn't work if its writers didn't know how to write Associated Press copy, "Weird Al" Yankovic's music wouldn't work if he and his band were incapable of mastering the sound of just about any song imaginable. There's another immutable rule in place when it comes to "Pancreas": You can't re-create the ornately masterful compositions of Brian Wilson without being genuinely gifted yourself. This wonderfully crafted, wittily arranged biology lesson provides an excellent occasion to hail Yankovic's long-serving band: Jon "Bermuda" Schwartz (who, as noted above, has played with Weird Al since 1980) on drums, Steve Jay (1982) on bass, Jim West (1983) on guitar and latecomer Rubén Valtierra (1992) on keyboards. Together, they transform a frothy trifle into a masterclass.
11. "Yoda," Dare To Be Stupid (1985)
(Parody: The Kinks' "Lola")
This is another one of Yankovic's earliest parodies, dating all the way back to 1980, when Yoda made his debut in The Empire Strikes Back. By the time an official version was finally released — after years of wrangling to get permission from Ray Davies and George Lucas — the source material (The Kinks' "Lola") was 15 years old. Yet "Yoda," which is sung from Luke Skywalker's perspective, still endures as a counterpoint to the idea that every "Weird Al" Yankovic song has to provide a rapid response to a present-day pop-cultural moment. It helps that Star Wars is eternal, a fact "Yoda" acknowledges: "The long-term contract I had to sign / Says I'll be making these movies till the end of time." (Mark Hamill made his last movie appearance as Skywalker in 2017, so Weird Al was onto something.)
10. "Trapped in the Drive-Thru," Straight Outta Lynwood (2006)
(Parody: R. Kelly's "Trapped in the Closet")
It's hard to separate anything R. Kelly-adjacent from Kelly himself, so you'd be forgiven if you wish to skip an 11-minute parody of the wildly overwrought song series Trapped in the Closet. "Trapped in the Drive-Thru" is one of many Trapped parodies that floated around in the mid-'00s, but that hardly made the original easy to satirize; it's not as if Yankovic was going to come up with something more ludicrous or salacious than the yarn Kelly spun. So Weird Al tilts his song in a more mundane direction — a night in which a routine trip to grab fast food spins out into greater and greater frustration — while maintaining every ounce of Trapped's fists-clenched urgency. Perhaps the greatest feat of all: It never gets dull for a moment.
9. "Word Crimes," Mandatory Fun (2014)
(Parody: Robin Thicke's "Blurred Lines")
"Word Crimes" pulls off a neat trick: It offers a funny and quotable takedown of common grammar mistakes, lampoons the nitpickers themselves and justifies the existence of Robin Thicke's "Blurred Lines" by stripping it of terrible ingredients such as misogyny and Robin Thicke. The result is both worthy of Schoolhouse Rock! and much meaner in its disposition, as Yankovic sprinkles in dyspeptic insults (ex: "You should know when / It's 'less' or it's 'fewer' / Like people who were / Never raised in a sewer"). It's funny, catchy and joke-dense, and it's even got lessons to impart — and, by hitting No. 35 on the Billboard Hot 100, it gave Weird Al a Top 40 hit for the fourth decade in a row. Only five artists accomplished that feat from the '80s to the '10s: Yankovic, Madonna, Michael Jackson, U2... and Kenny G.
8. "Hardware Store," Poodle Hat (2003)
(Original)
Yankovic has never performed this one live, even though it's a fan favorite. Why not? Because it's basically impossible to pull off: The song is too intricate, its harmonies are too precise and its line readings require too much speed and dexterity to be re-created on stage with any regularity. This is a glorious song, with an arrangement that properly mirrors the intense enthusiasm our narrator feels for, well, the opening of a new hardware store in his area. Weird Al's discography is peppered with songs that hurl high praise at some mundane household item, foodstuff or profession. "Hardware Store" is the best of them all.
7. "Eat It," In 3-D (1984)
(Parody: Michael Jackson's "Beat It")
Michael Jackson is a complicated figure, to put it mildly, but he had an unmistakably profound impact on Yankovic's career. His "Beat It" inspired Weird Al's first Top 40 hit in 1984, his "Bad" got re-created as "Fat" a few years later, and his refusal to grant permission for a "Black or White" parody called "Snack All Night" paved the way for Yankovic's early-'90s comeback. (After Jackson's said no to "Snack All Night," Yankovic cast around for an alternative, just in time for "Smells Like Teen Spirit" to hit big. There's no way another food-based Jackson retread would have done for Weird Al what "Smells Like Nirvana" did.) And the thing is, "Eat It" still holds up, even after nearly 40 years and a zillion other food-related parodies. It even provided a vital public service in the early days of the pandemic, as an assortment of actors and comedians performed the song in the style of Gal Gadot's "Imagine" disaster, just to remind the world of a simple truth: We're all in this together.
6. "Dare To Be Stupid," Dare To Be Stupid (1985)
(Parody: Devo)
Yankovic has done dozens of pastiches — or style parodies, depending on which terminology you prefer. None shine as brightly as a Devo tribute that feels an awful lot like a top-of-the-line Devo song. As a Weird Al mission statement, "Dare To Be Stupid" fits perfectly alongside Devo's theory of de-evolution, doing right by parodist and subject alike. Blending subverted aphorisms ("Bite the hand that feeds you / Bite off more than you can chew"), non sequiturs ("Stick your head in the microwave and get yourself a tan") and references to old TV commercials ("You should squeeze all the Charmin you can while Mr. Whipple's not around"), "Dare To Be Stupid" is deeply, lovably silly, even as it hints at deeper truths about life's absurdity.
5. "I Lost on Jeopardy!," In 3-D (1984)
(Parody: The Greg Kihn Band's "Jeopardy")
You want a sense of how long "Weird Al" Yankovic has been doing this? His song about Jeopardy! predates Alex Trebek's entire 37-season run as host. Instead, it's 1970s host Art Fleming who gets referenced in the song — "Art Fleming gave the answers / Oh, but I couldn't get the questions ri-i-ight" — and appears in the hilarious video alongside original announcer Don Pardo. "I Lost on Jeopardy!" parodies a 1983 song called "Jeopardy" by The Greg Kihn Band, whose hit-making days dried up shortly thereafter; it's fair to say that Yankovic's parody has overshadowed its subject in the public's imagination. But that's not really fair to Kihn, who remains active and was, after all, a good enough sport to appear in the "I Lost on Jeopardy!" video. The song is just too funny to be denied — and, seriously, watch the video if you haven't seen it.
4. "Amish Paradise," Bad Hair Day (1996)
(Parody: Coolio's "Gangsta's Paradise")
And now, to run down the entire list of serious controversies in Yankovic's epic comedy career:
1) He thought he'd gotten Coolio's permission to parody "Gangsta's Paradise," but it turned out he hadn't and Coolio was mad.
That's Yankovic's dark side, right there, which helped make for one of the most amusingly boring episodes of VH1's Behind the Music ever made. But even this story has a happy, albeit bittersweet, ending: The two had apologized and reconciled years before Coolio's death in 2022 — Coolio spoke of the subject humbly and graciously in self-effacing interviews — and Yankovic posted a sweet tribute on social media.
As for "Amish Paradise" itself, Coolio got it right in 2014: "It's actually funny as s***." The whole concept is right there in the title, and yet every moment of the song builds on it, piling on gags from every possible angle. And the video, with Florence Henderson as our narrator's "very plain" wife, is basically perfect.
3. "Smells Like Nirvana," Off the Deep End (1992)
(Parody: Nirvana's "Smells Like Teen Spirit")
New 12-year-olds are minted every minute, bringing with them a fresh zeal for Weird Al's music. But new 20-year-olds are minted every minute, too, bringing with them some of their earliest pangs of nostalgia for the music of their childhood. So it shouldn't have come as a surprise that "Smells Like Nirvana" activated both demographics (among others), sparking the first of many Weird Al comebacks. Still, this was the big one: the first clear sign that Yankovic wouldn't fade into the cozy obscurity of I Love the '80s flashbacks. The song marks a creative reinvigoration for the singer and his band, who combine to mimic Nirvana flawlessly amid funny commentary on the inscrutability of Kurt Cobain's lyrics. Like "Perform This Way" (see No. 15, above), this is a song parody that also serves as a larger-scale meta-commentary on the artist who made it possible. As such, it perfectly captures its moment in pop history, even as it helps reshape it along the way.
2. "One More Minute," Dare To Be Stupid (1985)
(Original)
The first joke takes a full 50 seconds to materialize. Amid a light-and-breezy doo-wop arrangement, Yankovic spends the song's opening moments establishing that his lover is leaving him, and that he's responded by tossing keepsakes and losing her number. Then, the first twist: "And I burned down the malt shop where we used to go, just because it reminds me of you." Then, a bit more doo-wop.
From there, without breaking format, the song gets weirder and more visceral. The topic shifts, inevitably, to a series of tortures he'd be willing to endure rather than spend one more minute in her company — from the relatively mundane ("I'd rather get my blood sucked out by leeches") to object lessons in how to paint pictures with words ("I'd rather jump naked on a huge pile of thumbtacks / Or stick my nostrils together with crazy glue").
It all adds up to a remarkably cathartic experience. "One More Minute" is not only the greatest Weird Al original, but also a truly great breakup song, period. And, though the reference has fallen out of date, I'm not sure there's a better gag in Yankovic's arsenal than the one found in these simple words: "I'm stranded all alone in the gas station of love / And I have to use the self-service pumps."
1. "White & Nerdy," Straight Outta Lynwood (2006)
(Parody: Chamillionaire's "Ridin'")
There are lengthy stretches of this Chamillionaire parody, which gave Yankovic his first and only Top 10 hit, in which jokes land at a rate of one every 1 to 2 seconds. Cumulatively, it's funny enough to make you dizzy as the gags geyser forth:
First in my class here at M.I.T.
Got skills, I'm a champion at D&D
MC Escher, that's my favorite MC
Keep your 40, I'll just have an Earl Grey tea
My rims never spin — to the contrary
You'll find they're quite stationary
All of my action figures are cherry
Stephen Hawking's in my library
Those eight lines speed by in 13 seconds.
This is a song by nerdiness, of nerdiness, for nerdiness; it's meant to be picked apart, line by line, and studied. Yankovic even loaded its video with fresh Easter eggs for devotees to locate, annotate and fuss over; the fact that Key & Peele show up, pre-superstardom, is just a lucky bonus for a song that never stops getting everything right all the time.
Yankovic is legendarily devoted to craft; he's known for compiling countless jokes for each song in binders and then culling all but the best ones. So "White & Nerdy" was perhaps destined to be his greatest song: He himself is white and nerdy and, as with so many great writers, he's in top form when documenting the world he knows best. Also, at the risk of sounding extremely white, and also nerdy, he's a pretty damn good rapper.
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