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#25 Arcade Fire

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Another "moment in time" band for me. In late 2003, frustrated with many areas of my life, and about to hit 30, I quit my job without a new one (this is way before it was hip/safe to do so) and spent a year volunteering for John Kerry's presidential campaign. When Kerry lost, and my dreams of moving to the West Wing vanished, I headed to......Myrtle Beach, South Carolina.... for a few months to work in a family restaurant. As I tried to re-engineer what to do with my career, a call came from a recruiter in "Mountain View." A company was looking for someone with skills loosely related to what I'd done for the first 6-7 years of my career, but moving more into digital. A few weeks later, I was boxing up my stuff in Brooklyn and heading to the Bay Area. Upon arrival, I found a place in Sunnyvale and for the next year, prior to moving to SF, spent most of my free time either at the gym, in a Barnes and Noble or buying records. And with the move, I was looking ...

#26 Gram Parsons

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Arguably the individual most responsible for alt.country movement that spawned many of my favorites, including Uncle Tupelo, Wilco, Son Volt, Old 97's, and on and on and on.... Favorite record : Grievous Angel (1974) Where are they now? Gram died of a drug overdose in the 1973 at the age of 26.

#27 The Band

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Arguably the best band ever to come out of the United States. Favorite record : Music From Big Pink (1968) Where are they now? The Band disbanded in 1976 as chronicled in the greatest music documentary of all-time, The Last Waltz .

#28 Gillian Welch

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What's that famous line about Nick Drake's music? Something about Nick's catalog sounding like "what you'd hearing upon stepping through the gates of heaven." Whatever it is, that pretty much sums up how I felt upon hearing Gillian Welch's first record, Revival , sometime in 1996. I listened to the first track, "Orphan Girl," about 20 times before even making it past that track. It honestly wasn't that far off from how I felt when I heard Springsteen for the first time, or Uncle Tupelo. It nearly knocked me over. Only a few months later, I saw Gillian Welch and David Rawlings open up for Son Volt at The Paradise in Boston, and it was everything I heard on record and more. Gorgeous melodies and phenomenal songwriting matched with Rawlings' breathtaking guitar chops. They closed the night, paired with the original Son Volt lineup, and blasted through a raucous take on Neil Young's "Come on Baby Let's Go Downtown." What...

#29 Steve Earle

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My timeline for interest in Earle is oddly almost exactly as #30 on this list, Damien Jurado. I discovered Earle in the early 90s, right before the best output of his career. Fresh out of the pen, Earle was sober, still young, and clearly hungry. The quick output of Train a Comin' (1995), I Feel Alright (1996) and El Corazon (1997) represents the epicenter of Earle's recorded output and fit perfectly with the alt.country movement that was ballooning at the time. In addition to these masterful records, Earle was also running E-Squared Records, where he introduced the world to the likes of The V-Roys, 6 String Drag, Bap Kennedy and Cheri Knight. All four of those remain among my favorites of that period, and Earle's impeccable ear and desire to raise awareness to these acts is something I'll forever cherish. Favorite record : I Feel Alright (1996) Where are they now?  I can't claim to follow much anymore, but Earle's out there still touring and making re...

#30 Damien Jurado

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There are points in your life when a certain act or sound just fits a period of time. I discovered Damien Jurado in 1999 when he released the fantastic Rehearsals for Departure . And I was off. For a solid decade, through to 2008's Caught in the Trees , I was hooked. If you look at my last.fm from that period, Jurado checks in at #7. For reasons I can't really explain, I then abandoned ship. Jurado has released four records since, and with a few exceptions, I've been on the sidelines. But tonight, as I listen to 2003's Where Shall You Take Me?, I'm reminded. These songs are gut-wretchingly gorgeous. On the level of Nick Drake or Elliott Smith. At times, better. And just like that, I'm back. Maybe it's time I explore those four new ones. Favorite record : Where Shall You Take Me? (2003) Where are they now? Still out doing his thing...

#31 Aimee Mann

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There are few songwriters that I relate to more than Aimee Mann. The former Til' Tuesday singer has had a stellar solo career. I fell for Mann after seeing PT Anderson's phenomenal Magnolia in 2000. That movie wouldn't have had nearly the impact if not for Mann's soundtrack additions. The "Save Me" scene to close the film remains one of the most memorable scenes in film history. And well, here it is: 2005's The Forgotten Arm remains one of my favorite records of the past 20 years. For those keeping score, it was actually my eighth favorite record of the 2000s via Huffington Post . A concept album for the ages, Mann's mastery of the spoken word and chilling vocals to match is pure perfection. Bachelor No. 2 , Mental Illness , Smilers -- all albums with phenomenal moments. Aimee Mann is one of the best songwriters of our time. Or any time. Favorite record : The Forgotten Arm (2005) Where are they now? Still out there making great records...