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

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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.