9. Lit, A Place in the Sun (1999)
In 7th grade, I bought this CD on the strength of the admittedly still super-catchy “My Own Worst Enemy.” About a week later, after listening to the album in entirety a few times, I sold it to my friend Mike for $10. The upside was that I had at least cut my losses. On the downside, I lost a good friend that day.
8. Will Smith, Big Willie Style (1997)
I think everyone born between 1983 and 1990 owns Big Willie Style, but that doesn’t make it any less embarrassing. Everything about this record seemed like a real-life projection of what my dad mistakenly thought hip hop was, from the painfully lame album title to the cover featuring Will unironically adopting a Statue of Libertyesque pose with his button-up flapping majestically in the breeze. Big Willie Style is the CD that introduced the phrase “getting’ jiggy wit it” to the world, for Christ’s sake. Bonus embarrassment points: I originally bought Big Willie Style on cassette right before I got a CD player, and then repurchased it on CD afterwards. I think it was at that exact moment that God decided I wasn’t allowed to lose my virginity for another ten years.
7. Papa Roach, Infest (2000)
Usually I can reconnect with my guilty pleasures of years past, but I can never recapture my brief, but passionate love for Papa Roach’s breakout hit “Last Resort.” I still remember hearing it for the first time on MTV and thinking it was so freaking badass – the crunchy riff, the screaming vocals, the goth angst video. It was everything 13-year-old me wanted, the audio equivalent of pro wrestling, pizza rolls, and lighting shit on fire in your backyard. And maybe it’s because, in retrospect, everything about Papa Roach is just straight-up hilarious (Coby Dick??), but I can’t even get a “those were the days” buzz from it now. Now it just seems like the audio equivalent of braces, acne, and 56k porn.
6. Sugar Ray, 14:59 (1999)
Most of the CDs on this list at least seemed like a good idea at the time, but I think I was embarrassed even as I handed the clerk my $15 for this one. He was probably all like, “You know this isn’t the one with ‘Fly,’ right?”
5. Mystikal, Let’s Get Ready (2000)
I used to find the lyrics to “Shake Ya Ass” hilarious, but the trove of unintentional comedy Mystikal once provided became a lot harder to laugh along with after he went to jail for a heinous case of sexual battery. But once, yesteryear, I used to feel undeniably stirred upon hearing such lovestruck musings as, “I’m buyin’ if you got nice curves for your iceberg,” or “I like my women fire like CAY-ENNE!!/Chocolate and bowlegged – when I’m runnin’ up behind her!!” Honestly, until looking it up just now, I always thought he was yelling “chocolate and bowling,” which sounds way more fun.
4. The WWF, WWF The Music, Vol. 3 (1998)
Yes, this is just a collection of wrestling entrance songs for late-90s WWF (now WWE) wrestlers like Steve Austin and The Undertaker. And you know what, I’m not apologizing for this one – wrestling entrance music is the pinnacle of human achievement. If I ever get a job that allows me to begin my workday by strutting into the office to the accompaniment of second-rate guitar riffs while I tear off my shirt and tell everyone to “suck it,” I’ll know I’ve made it. I’m kidding about the second-rate guitar riffs, by the way, and I’m 100% not kidding when I say this is probably the musically accomplished album on this list.
3. Kid Rock, Devil Without a Cause (1998)/The History of Rock (2000)
The double-dip is what makes this one particularly egregious. Pretty much every other boy at my school bought Devil Without a Cause on the strength of “Bawitdaba” and “Cowboy,” songs that sounded the way Mountain Dew Code Red tasted. But The History of Rock, released two years later, isn’t even a studio album – it’s a few new songs rounding out a collection of the “best” of Kid Rock’s earlier, pre-fame albums, a desperate attempt to cash-in on his new success with some crap they had laying around. Admittedly, it’s a great album for people who like song titles written in text-speak (“Born 2 B a Hick” and “Fuck U Blind,” the latter of which I can only imagine is a tragic, Oedipal ode).
2. Smash Mouth, Astro Lounge (1999)
Even though it’s listed at #2, I think this actually might the most embarrassing entry on the list. Even the album title and cover, featuring some kind of cheesy outer space motif, look like they were created by someone who was like, “God, Smash Mouth is lame as fuck.” What was it about “All Star” that temporarily convinced the world that Smash Mouth should be allowed to play during anything other than a Shrek movie montage?
1. Limp Bizkit, Significant Other (1999)/Chocolate Starfish and the Hot Dog Flavored Water (2000)
Again, the fact that I went back for seconds is what takes Limp Bizkit to the top of this list, amongst other reasons. I’ve inexplicably written two more articles about Fred Durst than anyone should care to write post-2000 (here and here), but 15 years later I still can’t wrap my head around the guy. Was he trolling us all with his near-illiterate rhymes and juvenile puns? Was he a lab experiment gone wrong, some kind of Floridian caveman created by perverse nu metal engineers and fueled by Natty Light and tribal tattoos? I’m not sure, but I still hold to a rarely espoused theory that Limp Bizkit could’ve been a really fun band with literally anyone else at the helm. But perhaps it’s better this way – fun bands are forgotten, but Limp Bizkit will live on forever as a testament to the stupidity of middle schoolers everywhere.