The great thing about the iTunes Store is that you can buy just about any song you can imagine, cheaply and easily. And the worst thing about the iTunes Store? Sometimes you can buy those songs a little too easily.

Apple's retail store for digital downloads has been open for a decade now, and in that time, you've probably loaded up on a lot of music. And you don't have to tell us that some of those downloads probably seemed like a good idea at the time. In honor of the 10th anniversary of the iTunes Music Store, I combed through my purchase history to find some of the instances where I could have spent my 99 cents more wisely. Perhaps my confessions of regrettable musical choices will make you feel better about your own iTunes indiscretions over the last 10 years. At the very least, I hope my embarrassing selections serve as a reminder that when it comes to hitting that download button in Tunes, sometimes discretion is the better part of valor.

More One-Hit Wonders Than I Can Count

Just after the iTunes Store opened its virtual doors, my paymasters at Macworld wanted an article on the depth and breadth of the store's initial offerings. Among the more hare-brained of my assorted schemes to survey the store's selection: See how many of VH1's Top 100 One-Hit Wonders I could download from iTunes. The answer, at the time? 39. The cost to my psyche whenever "It's Raining Men" has popped up on random shuffle during the ensuing decade? Incalculable.

"Wait, you went ahead and actually downloaded all those songs?" you may be asking. "Why not just keep a running tally and leave it at that?"

Because I am devoted to my craft.

"Well, fine. So why keep them in your iTunes library all this time?"

Because shut up is why.

Besides, there are a few enjoyable tunes among those 39 otherwise regrettable downloads. Hearing the occasional "Tainted Love" from Soft Cell or "Come On Eileen" from Dexy's Midnight Runners more than makes up for the random appearances by Vanilla Ice crooning "Ice Ice Baby" or The Divinyls offering up their musical tribute to onanism with "I Touch Myself." (That's a fun conversation to have with HR, by the way.) And it could have been worse: As committed as I was to downloading every one-hit wonder I could, I blanched at paying 99 cents for Billy Ray Cyrus's "Achy Breaky Heart." I wish I could travel back in time and shake the hand of the 2003 version of me.

You Light Up My Life

There is one last item from L'Affaire One-Hit Wonder that I hesitate to mention, largely because it reflects poorly on me. VH1's list of now-you-see-'em-now-you-don't musical sensations includes "You Light Up My Life," the title song from the forgettable movie of the same name. It is a treacly, drippy ballad in which singer Debby Boone fails to bring the raw, unbridled energy her father Pat used to bring to those Chevrolet ads. It also won an Academy Award for Best Original Song, proving that the late 1970s really were the age of malaise.

Anyhow, Debby Boone's version wasn't in the iTunes Store when I wrote that one-hit wonders article. (It is now, you lucky people.) Undeterred--and for reasons that remain a mystery a decade later--I bought an instrumental version of "You Light Up My Life". Because, obviously, once you strip "You Light Up My Life" of its vocals and lyrics, you've improved the song immeasurably.

On a Bicycle Built for Joy (Raindrops)

In 2010, Apple extended song previews in the iTunes Store to 90 seconds for songs longer than 2 minutes and 30 seconds--a welcome change for those of us who want to know just what the heck we're getting ourselves into when we part with our hard-earned 99 cents. Oh sure, iTunes always offered 30-second previews of songs, but that was hardly enough time to figure out if the musicians were on their best behavior right up until the moment those 30 seconds were up.

Case in point: This version of "Raindrops Keep Falling on My Head" from the Butch Cassidy and the Sundance Kid soundtrack. I have pleasant memories of that song from growing up, when my mother would sing it to me whenever I was feeling glum (which is to say, she sang it frequently). And indeed, this particular rendition offers just the right note of wistfulness--right up until the 1:29 mark where the song takes a sudden 180-degree swerve into a bouncy, 1970s-style ragtime orchestration that sounds like the sort of thing one would hear at a clown's funeral procession. This continues for nearly a full minute--perhaps B.J. Thomas had excused himself to grab a glass of water--before Burt Bacharach's Groovy Good-Time Band finishes killing the mood and we resume with our regularly scheduled ruminations on how my eyes won't be turning red 'cause crying's not for me. But crying is most certainly for me, at least now that I had to endure that.

Had 90-second previews existed when I downloaded "On a Bicycle Built for Joy (Raindrops)," it is likely I would never have paid good money to hear a beloved childhood memory brought to its knees. Instead, the song remains in my iTunes library as a reminder that raindrops falling on one's head is the least of one's troubles.

Love Boat

I host an occasional segment of the Macworld Podcast called the Macworld Pundit Showdown. There are funny sound effects and thematically appropriate musical snippets played throughout, and we all have a good time recording it. Presumably, a fraction of the listening audience enjoys it as well. Anyhow, those songs have to come from somewhere, so I buy them off of the iTunes Store.

I'm mentioning this in case I unexpectedly slip off this mortal coil, and my next-of-kin, when going through my effects, discovers that I have a copy of the theme song from The Love Boat performed by something called The South Bay Groove System. Please alert my heirs that the song was specifically downloaded for this podcast episode and not because I secretly harbor dreams of hanging out with Gopher and Isaac on the Lido Deck.

Not after how they treated Julie the Cruise Director, I don't.

Iron Man

There's a lady-or-the-tiger quality to live versions of songs. Maybe this is the moment when it all comes together for the band--when the music and the vocals blend so seamlessly, when the energy of performing before an arena full of devoted fans--elevates a known commodity to new heights. Or perhaps the band is preoccupied with the thought of all the groupies waiting back at the after-party and rushes through the song with casual indifference. I leave it to your imagination as to where on that spectrum this Black Sabbath recording of "Iron Man" falls.

I'm not sure why I bought a copy of "Iron Man," other than it must be some federal regulation that every adult male between the ages of 30 and 60 must own that particular song. I don't know why I bought this particular version, though I hope it was because it was the only available copy of "Iron Man" on iTunes at the time. I do know I wish I had previewed the track first so that I would have learned that this particular edition of Black Sabbath was fronted by Ronnie James Dio and not Ozzy Osbourne. (I once asked no less of an authority than Jim Dalrymple for his opinion of the Ronnie James Dio-led Black Sabbath. "It serves its purpose," he said, before returning his attention to his Heineken.) About halfway through the song, Dio goes deliriously off-script and begins improvising lines, one of which is "I'm coming to claim your soul." It took me several dozen close listenings before I realized he wasn't singing, "I'm coming to clean your shelves."

Which is disappointing because I thought that was a very gracious offer by Ronnie James Dio.

My Way (DJ Lethal Remix)

I will not apologize for owning a Limp Bizkit song--it has a nice driving beat that lends itself to workouts. I will, however, wonder why I opted for the "Clean" download. "Listen to Fred Durst's incorrigible potty mouth?" I probably said as I clicked the Download button from my fainting couch. "Not on my watch."

And so, when I ride my exercise bike, and "My Way" comes up on the rotation, I'll be pedaling along, picking up the pace as Fred Durst's voice begins dropping out intermittently--the sound of iTunes sparing my ears the shock of Limp Bizkit's blue language. Indeed, there is one part of the song where the sound drops out for nearly four seconds, as Mr. Durst draws out every last syllable of his vulgarity. That is some professional-level cursing, folks.

The entire Rio album

Chances are you have a wife or husband or significant other with whom you've decided to build a life together. Bank accounts, legal affairs, earthly possessions--all these are combined under one roof because hey, we're all in this together. But keep your iTunes accounts separate, friends, or else you might find yourself having some uncomfortable conversations about each others' musical taste. Because one day a cut from Duran Duran's Rio album comes up randomly in iTunes's shuffle mode and you say aloud "I don't remember downloading this dreck." And then you will look up and see the love of your life--a woman who went to bed every night of her adolescence under the protective gaze of posters featuring Simon Le Bon, Nick Rhodes, and assorted Taylors--glaring back at you. It is then that you will realize that she is the reason you're the not-so-proud owner of "Last Chance on the Stairway." And there is no worse feeling.

Or so I've heard from a friend of mine.

This cheese stands alone?

Surely, I thought as I wrote this article, I can't be the only normally crafty consumer whose good sense evaporates in the face of Apple's remorseless download apparatus. So I pinged my colleagues: Were there any songs they had downloaded from the iTunes Store over the past decade that maybe didn't seem like such good investments in retrospect? Most of my Macworld cohort stood mute, the cowards. But a few brave souls joined me in publicly coming clean about their questionable judgment.

Here's what Christopher Breen had to say:

Unlike some of your regrets, I downloaded The Steve Miller Band's "The Joker" knowing full well that other than its delightful lifting of "the pompatus of love" from The Medallions' "The Letter," it's a terrible ear worm of a tune. Everything from the "from what weird reggae record did they pull that bass line?" ponderings to the obnoxious "woot-woo!" guitar ejaculation screams "Damn you to hell for putting that in my brain, Steve Miller!"

Why purchase it then? I'm ashamed to admit that I did it to torture my wife. When things get testy around the house, you can count on me blasting "The Joker" from end to end. Fair fight? Not on your life.

And here's Dan Moren's contribution to our public confessional:

"Accidentally In Love" by Counting Crows. I mean, what can you say about a song with "accidentally" in the title? The year was 2004, and I think I'd recently seen Shrek 2, in which this Counting Crows song figured prominently. While perhaps not as egregious as Smash Mouth's cover of the Monkees' "I'm a Believer" from the first movie in that series, "Accidentally in Love" quickly lost its charm as an earworm and instead became a grating reminder to be more careful about what songs I spend my 99 cents on.

And finally, we turn to Jason Snell for the last word:

Anything I ever downloaded from Glee. All the Glee. Simply Glee.

See also:

iTunes secures lead over competitors in digital TV download market

Apple's iTunes hits record revenues as 10th anniversary approaches

Why Apple should fix the way iTunes Store purchases work

Average UK iTunes account is worth £345, new study finds