“Leader of the Pack” by the Shangri-Las

There were a surprisingly large number of melodramatic teenybopper songs about tragic deaths in the late Fifties and early Sixties, and none of them have aged particularly well, but this one seems to have held up better than the others—at any rate, it’s certainly the only one you still occasionally hear in a non-ironic context nowadays. It’s still melodramatic and goofy, but it’s far catchier than most of its peers, it isn’t as blatantly stupid as items like “Teen Angel” or “Running Bear”, it doesn’t have the air of smug detachment than singers like Dickey Lee brought to these kinds of songs, and its extreme lyrical dissonance actually sounds like it might have conceivably been done on purpose. More importantly, this particular song was, by songwriter Jim Steinman’s own admission, the direct inspiration for Meat Loaf’s unforgettable classic “Bat Out of Hell” almost two decades later, so clearly some good has come of this song’s existence.

Verdict: Okay, I guess, but mostly just by the standards of its genre (and the inspiration it provided to Steinman, obviously)

“Hollaback Girl” by Gwen Stefani

This is an extremely weird song as well as a bad one, built around an obscure slang term that people are still debating the meaning of ten years later, and with an out-of-nowhere cheerleading chant in the middle loudly proclaiming a totally random word. This song was the work of star producers the Neptunes, who basically recycled the same talky, staccato vocal style they used on the equally annoying “Milkshake” the year before, and when you combine that with the nonsensical lyrics, you get a song utterly devoid of any kind of point.

Verdict: Bad

“Tubthumping” by Chumbawamba

This song mostly gets hatred from people who simply don’t understand it. Chumbawamba were an extremely political band, and this commercial experiment is no exception. The political content is subtler, veiled just beneath the surface, but this is far more than just a generic drinking song. The triumphantly raucous chorus of “You’re never gonna keep me down”, the snatches of old folk songs between the verses, the atmosphere of a rowdy tavern where the people sing ‘the songs that remind him of the good times’…not to mention the very unambiguous spoken message in the intro to the album version…paint a picture of the unbreakable spirit of the common man. If you’ve ever read George Orwell’s 1984, think of the scene where Winston realizes that in a world where the ruling class have been turned into brainwashed lunatics, the Proles have retained their humanity, and that however stupid and vapid they seem, their love and loyalty to each other ultimately renders the Party’s victory null and void, and you have the right idea.

Verdict: Good, but you need a little context to understand why

“Hold My Hand” by Hootie and the Blowfish

Hootie and the Blowfish get a fair amount of scorn from the rock-snob set because the followed the model of their Easy-Listening predecessors more than most other Adult Alternative bands, but their music ranges from okay to really good, and this one is easily their best. It has a soulful, almost bluesy quality that didn’t really show up that much in their other work, and it does a great job of showing off Darius Rucker’s marvelous voice, which was always the band’s biggest asset.

Verdict: Good

“We Are All On Drugs” by Weezer

This song’s main problem is that it is totally lacking in the appealing qualities we normally associate with this band. Weezer are, above all else, known for their catchiness; even their most serious and ambitious album, Pinkerton, is loaded with melody. But this song is harsh, tuneless and belligerent, which, combined with its pessimistic harangue of a lyric, makes it perhaps the most unappealing song this band has ever done.

Verdict: Bad

“The Candy Man” by Sammy Davis, Jr.

I’ll never understand why this wonderful song gets included on so many ‘Worst songs of all time’ lists. I guess it’s mostly because it’s essentially a showtune (having been written for a musical children’s movie by veteran Broadway songwriters), and was a massive radio hit at a time when Rock snobs’ contempt for anything that suggested Broadway or Great American Songbook-era pop was at its zenith. But this is a gloriously sunny and delightful gem sung by one of the great popular singers of the century, and there’s no real reason it should still have a negative reception today, especially now that the movie it comes from is a beloved classic.

Verdict: Good

“Ode to Billie Joe” by Bobbie Gentry

Bobbie Gentry was the female answer to the ‘Outlaw’ Country artists like Johnny Cash and Willie Nelson, a voice of pure visceral artistic truth in an era when Nashville polish, while nowhere near as bad as it is now, still sometimes stifled the kind of rawness Gentry represented. This song is dark, depressing, and deliberately ambiguous, leaving the listener to draw his own conclusions about what motivated the title character’s suicide and what the narrator’s real relationship was to him. It’s a brilliant and disturbing piece of work, probably too disturbing for a lot of the Country music audience, but still as fascinating and evocative today as it was then.

Verdict: Good

“My Way” by Frank Sinatra

This song’s biggest liability is that the English lyrics (the song was originally in French) were written by Paul Anka, who, as “You’re Having My Baby” clearly shows, was not exactly a lyrical mastermind. When you hand it to a truly great figure in music like Sinatra or Elvis who can justify the sentiments the song is built around, it simply works, so well that the clumsy lyrics become a non-issue. Give it to Anka himself or any other mere mortal singer, however, and it becomes simply a mediocre-to-poor song with a vast reputation it cannot possibly live up to.

Verdict: It depends entirely on who is singing it.

“Macarena” by Los del Rio

There have been a lot of dance crazes that look really stupid in retrospect, but this song has retained a special hatred as the years go by, and is one of the few novelty songs from past decades to remain almost universally hated. This isn’t because of the dance itself…plenty of other songs connected to stupid-looking dance crazes have become affectionately-regarded nostalgic classics (e.g. “The Funky Chicken”). It is entirely because of the music itself, a maddeningly irritating earworm that is catchy in the absolute worst sense of the word, and would be one of the worst hit songs of the Nineties with or without its accompanying novelty dance.

Verdict: Bad

“Itsy-Bitsy-Teenie-Weenie Yellow Polka Dot Bikini” by Brian Hyland

This song has certainly stuck around, but it isn’t really all that good even by the standards of the Novelty Song genre. It was a clear rip-off of “The Purple People Eater”, but had none of that song’s bizarre humor, and the hook is legendarily irritating, sort of the “Macarena” or “Barbie Girl” of its day.

Verdict: Bad