“Freeborn Man”– Junior Brown“I’ve been listening to Outlaw Country on satellite radio, and this guy’s stuff kills me. I saw him live in college, and he was even more amazing. Simple honky-tonk stuff but incredibly well-executed.”

“To Beat the Devil”– Kris Kristofferson“Actors who are singers – why is that the only ones who are good at both are country guys? Kristofferson has a pretty great catalog. I like this song for its last line.”

“I Am Trying to Break Your Heart”–Wilco“This is my favorite song from my favorite band. Hands down. There are a lot of things Wilco does well, and they all of them on this song.??

“Time of the Preacher”– Willie Nelson“The idea of a ‘country concept album’ is weird enough, but in 1975 when country was languishing under the overproduced “Nashville Sound”, Willie Nelson released exactly that. It’s spare and beautiful and gets at the heart of good country music. Simple, effective, emotional storytelling.”

“Wayne Coyne deserves some kind of lifetime achievement award for being willfully, boisterously abstract and arty. But when their stuff hits, it hits hard. Iron and Wine did a great cover of this too.”

“Man, these guys sound cool together. Husband-and-wife duo! Everytime I hear this on the radio I turn it up.”

“There is a simplicity to this song (and this band) that disguises its innovation and depth. The fact that this band produced two equally kickass bands is testament to just that.”

“Los Lobos are wild, weird, raucous, and heartfelt; decidedly not just another band from East L.A. Also, bonus points for the awesome video, which predated Coraline’s visual aesthetic by two decades.”

“This is an all-star team of a band: virtuosos at every position and two crazy perfectionists at the helm. This song has my friend’s favorite line in it: ‘Is there gas in the car? Yes, there’s gas in the car.’ Get going.”

“Not only were these unassuming guys from Queens super-laid-back and cool with their jazz-heavy samples (in an era of Public Enemy and BDP-style militant politicizing and West Coast N.W.A gangstaism), they also introduced Busta Rhymes to his widest audience yet. Well-played all around.”

“B.O.B. (Bombs Over Baghdad)”– Outkast“‘Player’s Ball’ and ‘Rosa Parks’ turned me on to OutKast, but this is the first OutKast single I heard that really put them over the top for me. Crazy, frenetic, kinetic beats that presaged an amazing and truly original career.”