5 Fantastic Albums Released 25 Years Ago This Month

It’s an interesting batch of albums that emerged in August 1999. That era was one when many legends were taking stock of their legacy, and two of the albums on this list find veterans looking back and spotlighting their songwriting abilities with acoustic renderings of their best songs.

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One of the most successful country albums of all time also came out of this period, while two less-heralded but ridiculously productive acts came out with stellar full-length releases of new material. Here are five albums from August 1999 that are definitely worth revisiting.

Fly by Dixie Chicks

Having worked their way up through independent labels, the Dixie Chicks (since rechristened as The Chicks) were ready for their close-up when they made it to the big leagues on their 1998 major-label debut Wide Open Spaces. When Fly arrived in ’99, the floodgates really opened, with single after unforgettable single climbing the country charts. Listening to it now and comparing it to the Nashville sound of today, it’s striking just how much Fly sounds more like what we now consider alt-country, from the smart songwriting throughout to the focus on reserved, tender arrangements, and the trio’s inviting vocal blend.

Mock Tudor by Richard Thompson

Because he’s so consistent in the quality of his releases, individual LPs within the Richard Thompson catalog are almost underrated, as people focus on the greatness of the whole. There’s not a wasted moment among the dozen songs on Mock Tudor. Thompson rocks out a bit more on the album than on others surrounding it in his timeline. “Hard on Me,” for example, recalls the fireworks he brought on “Shoot Out the Lights.” One thing that didn’t change: The writing was as sharp as ever, with the mournful “Dry My Tears and Move On” standing as one of his best slow ones.

Do the Collapse by Guided by Voices

Robert Pollard’s beloved indie-rock outfit Guided by Voices stands out for their ability to crank out a certain type of no-frills power pop with relentless regularity. Ric Ocasek, the Cars’ mastermind, was known for offering plenty of frills. That’s why many fans of the band balked at first upon hearing Do the Collapse, whereby Ocasek’s production throws a little bit more bombast into the equation. Perhaps the best way to view this album then is as a gateway for those who don’t know much about Guided by Voices and can get acclimated to Pollard’s melodic chops on winning tracks like “Hold on Hope” and “Wrecking Now.”

Rough Harvest by John Mellencamp

Like many artists who have been around a while and enjoyed major success, Mellencamp has been anthologized with various greatest hits packages many times over. But Rough Harvest might be the best overall survey of his career-long excellence as a songwriter. Why? Perhaps because Mellencamp chose the material, skewing toward favorites (but not big hits) like “Jackie Brown” and “Minutes to Memories.” And by recasting them all in simple acoustic arrangements, he highlights the tuneful qualities that are often overlooked by those assessing his work.

The Austin Sessions by Kris Kristofferson

Perhaps because he’s a multifaceted guy who was able to play the acting game so well, it sometimes feels like Kris Kristofferson’s skills as a songwriter are underrated. You can’t possibly deny those talents upon hearing a collection like The Austin Sessions. Everything is stripped down to the bare bones of guitar and vocal here, except for a few choice mandolin or fiddle touches here and there and some special guests singing harmony. Aside from that, it’s just Kristofferson and his expressive croak going over classics (“Me and Bobby McGee,” “Sunday Morning Coming Down”) and should-be classics (“Nobody Wins,” “Please Don’t Tell Me How the Story Ends”) with heartwarming ease.

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