“I was asked to contribute a playlist and was initially excited, as one of the things I do in preparation for each new season of “Mad Men” involves putting together a list of songs that, in one way or another, inspire or inform either me or my character.

While I decided not to use either of those playlists (Season 1: WAY too much Taylor Swift; Season 2: Strangely all Usher), I did start thinking about our show and how it was passed over by many and not given a chance – dismissed before it had a chance to take shape at nearly every level, until of course it became a hit and won awards. I thought there are so many musical artists out there who, upon first glance, are no-brainers: hot pop tartlettes, smooth R&B guys, perfectly posed hip-hop sensations, wide-brimmed country twangs, and expertly slouched skinny “alternative” acts. I figured I’d make a list of the other side of the argument: people, bands, and acts whom in vacuum you’d look and say, “Nope, no way.” And then, “against all odds,” they make something beautiful, inspiring, and lasting. Enjoy.”

“Freeborn Man” by Junior Brown (Track 1) : “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.”
Listen to it here

“To Beat the Devil” by Kris Kristofferson (Track 2): “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.”
Listen to it here

“I Am Trying to Break your Heart” by Wilco (Track 3): “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.”
Listen to it here

“Time of the Preacher” by Willie Nelson (Track 4): “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.”
Listen to it here

“Waitin’ for a Superman” by The Flaming Lips (Track 5): “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.”
Listen to it here

“Gasoline and Matches” by Buddy and Julie Miller (Track 6): “Man, these guys sound cool together. Husband-and-wife duo! Everytime I hear this on the radio I turn it up.”
Listen to it here

“Screen Door” by Uncle Tupelo (Track 7): “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.”
Listen to it here

“Kiko and the Lavender Moon” by Los Lobos (Track 8 ): “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.”
Listen to it here

“Kid Charlemagne” by Steely Dan (Track 9): “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.”
Listen to it here

“Scenario” by A Tribe Called Quest (Track 10): “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. gangtaism), they also introduced Busta Rhymes to his widest audience yet. Well-played all around.”
Listen to it here

“B.O.B.” by OutKast (Track 11): “‘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.”
Listen to it here