Ask A Music Critic: What Is The Best Album Of 1999?

Uproxx Studios

Welcome to another installment of Ask A Music Critic! And thanks to everyone who has sent me questions. Please keep them coming at

Since you are doing a podcast about Woodstock ’99, what are your favorite albums of 1999? — Brian from Catonsville, Maryland

Before I answer that question, I just want to say that it has been far too long since the last “Ask A Music Critic” column. I just checked the archive, and apparently I haven’t written one of these since … August of 2018? What in the hell is the matter with me?! I wish I could say I was a perfectionist, and that I’ve been retooling this column extensively like it’s the next Wrens LP. But, honestly, I just lost track of time. I won’t let nearly a year go by before I mix it up with readers again, I promise.

Back to your question, Brian: I appreciate you remembering one of the only rules of this column, which is that I am guaranteed to pick your question if it presents an opportunity for me to plug myself. As Brian so kindly mentioned, I have a new podcast appearing exclusively on Luminary called Break Stuff: The Story Of Woodstock ’99. It’s an eight-part documentary for your ears about one of the great disasters in rock history. It includes interviews with dozens of musicians, promoters, attendees, security guards, EMTs, and many more. It debuted this week, and there will be new episodes every Tuesday through the end of August.

OK, end of plug. Now … my favorite albums of 1999! There are many ways to answer this question. If I were to, say, pick an album that most immediately evokes that year, I would probably say Eminem’s The Slim Shady LP, Moby’s Play, Santana’s Supernatural, or Limp Bizkit’s Significant Other. (1999 was a weird year!) If I were to choose the album I feel is most important, in terms of its artistic or critical legacy, I would go with The Roots’ Things Fall Apart, Fiona Apple’s When The Pawn …, or Magnetic Fields’ 69 Love Songs.

But if we’re strictly going with the album that I personally care the most about and/or find myself revisiting the most, it comes down to three choices: Wilco’s Summerteeth, Nine Inch Nails’ The Fragile, and Built To Spill’s Keep It Like A Secret.

I would likely rank them in that order of significance, too, though it’s so close that they’re practically interchangeable. Keep It Like A Secret screams “1999” to me so much that I can practically smell the dumpy house that I lived in during my junior year of college. The Fragile is an “important” watershed in the history of alternative rock, in that it helped to mark the end of that era. And Summerteeth is just an incredible artistic achievement, loaded with songs that move me to this day.

What do you think is the next genre of music to be “revived”? We’ve already seen funk, disco, ’80s pop, and ’90s indie rock receive varying degrees of pop culture re-appropriation and notoriety this decade. What do you think is next? — Gray from Los Angeles

My immediate thought after reading this question was chillwave, just because it’s been about a decade since it was the trendy form of indie. And there were probably a lot of 13 and 14-year-olds back then who loved Neon Indian and Washed Out who are now putting out their own records. But then I realized that chillwave at the end of the ’00s was a lot like disco at the end of the ’70s — the terminology eventually became outmoded, but the actual sounds seeped into the fabric of popular music to a profound degree. To my ears, a lot of contemporary indie music (and the sorts of “chill” playlists that are popular on streaming services) already sounds like chillwave, even if the word “chillwave” now seems horribly dated.

If I had to choose a genre or scene to actually come back, I’m tempted to stump for the art-folk sound of the late ’00s associated with Grizzly Bear, Bon Iver, and (kind of) Animal Collective. Again, it’s been over a decade since that stuff was really in vogue, so it’s ripe for rediscovery by a new generation (or a nostalgic revisiting by aging millennials). Also, don’t discount the power of the folk revival. It seems like we have one every other decade. It was on in the ’60s, off in the ’70s, on again in the ’80s, off again in the ’90s, on again in the ’00s, and off again in the ’10s. As we look ahead to the ’20s, I wouldn’t be surprised to see throngs of young people forsaking pop music, picking up acoustic guitars, and getting weird.

Is Coldplay due for a critical reevaluation? They’ve been a punchline for so long (Chris Martin is a meme machine, “conscious decoupling,” their generally pretty awful last few albums) that it’s overshadowed how interesting the first half of their discography was. Their first two albums are legitimately great and define the era to a certain degree and while their third album was a retread, they came back to do their fourth with BRIAN ENO and it’s totally great and interesting! Will Coldplay forever have the reputation of a punchline U2 ripoff band or are they going to grow in stature as we get away from the goofy dorkiness that they emanated? — Jason from Orlando

I think what you’re really asking is, “Will Coldplay ever be cool?” And the answer is no. For a certain kind of person, Coldplay will always be an irresistible target. They epitomize mainstream pop-rock more than any other act from the past 20 years, and mainstream pop-rock bands are the easiest music entities to mock. You will never be accused of cultural ignorance or insensitivity for glibly dismissing Coldplay. It’s presumed that there is nothing to “get” with this band, because the music is so easy to like. Though, if that were actually true, Coldplay wouldn’t be so polarizing.

The good news here (if you like Coldplay and especially if you’re Chris Martin) is that uncool popular rock bands always seem to endure. I’ve made this comparison before, and I still think it’s apt: Coldplay is the Journey of the 21st century. Like Coldplay, Journey was never cool. They made piano-heavy ballads about remaining faithful to their wives and girlfriends and their refusal to ever stop believin.’ Music critics labeled them corporate rock, but Journey fostered an incredibly loyal audience who stuck with them even when liking Journey seemed embarrassing. This is why Journey can still play arenas in 2019, in spite of their best-known singer being replaced by short Filipino man 12 years ago.

Being cool and popular tends put an expiration date on your career. Being uncool and popular makes you immortal. Coldplay will be immortal.

Since I was in high school, I’ve f*cking hated AC/DC. For some reason, their songs reminded me of these a**hole teenagers who would always drive their silly/loud/ridiculous cars around my hometown, just blasting Back In Black. But I recently revisited the album, and it absolutely kills. Has there ever been an album that you were angry to give a good review because you irrationally hated the band? — Christopher from Erie, PA

There was this singer-songwriter in the early ’00s who I absolutely could not stand. This person’s media persona was toxic — just really obnoxious and self-aggrandizing and annoying. Friends of mine loved this person, and would always push me to reconsider. For the longest time, I resisted. This person was just too big of a jerk. But, finally, I relented. I checked out an album. And, from the first song, I was hooked. This person soon became one of my favorite artists.

The album was Cold Roses. The artist was Ryan Adams.

Sometimes, it’s good to stick with irrational dislike.