Don Draper: The Mixtape

This story is a part of our Mad Men Takeover. Season four of the series premieres on AMC this Sunday, July 25.

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We’ve compiled a playlist based on our favorite suit-wearin’, womanizin’ ad man, Mr. Don Draper. Enjoy.

Jay-Z — “Big Pimpin’”
Donny D loves the ladies. Hova sympathizes: “Shit, I pause for nothin / y’all be frontin’ / me give my heart to a woman? / Not for nothin’ / Never happen / I’ll be forever mackin’.”

ZZ Top — “Sharp Dressed Man”
The fact that this video exists tells you everything you need to know.

Gil Scott-Heron and Brian Jackson — “Madison Avenue”
If you can get past all of Don’s various flaws, what you get—at least when he’s at the office—is a brilliant pitchman who could sell sand in the desert, Pepsi in Atlanta.

Punch Brothers — “Rye Whiskey”
Don is definitely a whiskey man, and Mad Men makes us nostalgic for the good ol’ days when you could get a little tipsy at board meetings. And he may be oh-so-urban in his Madison Avenue office, but we could see him getting down to this cut from the Punch Brothers’ latest, Antifogmatic.

James Brown — “It’s A Man’s World”
It’s a bit of a cop-out selection, yeah, but with all the sign-o’-the-times misogyny that goes down on that show (not to mention Draper’s own infidelity and treating his wife like crap), it was also sort of an inevitable selection.

Dave Brubeck — “Take Five”
Minus the womanizing and other various glaring flaws, Draper is a classy dude. He wears nice suits. He talks ever-so-smoothly when making those important pitches. And nothing says smooth and classy like this tasty jam from Dave Brubeck.

Neil Young — “Coupe De Ville”
“I got a Coupe de Ville / I got a bed in the house / where you once lived / I had a few cheap thrills / but they cost me a lot more / than I could give.” Yep.

The Beatles — “Nowhere Man”
Like the “Nowhere Man” in Yellow Submarine, despite all Draper’s great ideas and ambitions, his flaws always lead him to lonely ends. Also, he’s leading the life of another man. So really, Don Draper is nowhere, maaaan.

Frank Sinatra — “That’s Life”
Same general idea as “Nowhere Man.” “I’ve been a puppet, a pauper, a pirate / a poet, a pawn and a king / I’ve been up and down and over and out…” The perfect testament to Draper’s many lives.

OutKast — “So Fresh, So Clean”
Not just because of his sartorial prowess or general dopeness, but because of that line in the song about how “the sky is falling, no need to panic.” Even when all goes to hell (like the American Airlines crash in Season Two), Don keeps it together. Fine, Betty. Go to Reno.

Whitesnake — “Here I Go Again”
As we enter the fourth season, Don is leaving Sterling Cooper to start his own agency, Sterling Cooper Draper Pryce. Like a drifter, he was born to walk alone.