When Mad Men first hit AMC in July 2007, Don Draper and his Sterling Cooper cronies were working the advertising accounts of March 1960. But most of the notable music earmarked for that first season was Tin Pan Alley pop and exotica from the previous decade, still happily oblivious to rock ‘n’ roll and seemingly designed to make the protagonists’ past seem even more quaint and distant: a Frankie Lane polka from early 1951, a lightly swinging Rosemary Clooney nonsense novelty from 1952, an Yma Sumac mambo from 1953, a swooning Vic Damone croon from 1956. So when the season ended with Bob Dylan‘s “Don’t Think Twice, It’s Alright” — from 1963, even though the plot had only reached Thanksgiving 1960 by that point — it came as all the more of a jolt. The times they were a changin’, get it?

And of course they’ve kept changin’, as Mad Men has stumbled, swigged, puffed and philandered its way through six subsequent seasons and the rest of the ’60s. As this playlist (more or less chronological, by season if not within seasons) demonstrates, the show’s soundtrack has followed suit: from picture-perfect lounge dreaminess to twist hits and surf tunes and folk rock frets and frat rock frugs, and eventually to the psychedelic mind expansion of the Vanilla Fudge and Jimi Hendrix(“If 6 Was 9” — world turned upside down, get it?) circa Season 7, set in 1969. The music doesn’t advance in a straight line, exactly — middle seasons dipped back to 1955 for Tennessee Ernie Ford‘s “Sixteen Tons,” even 1930 for Maurice Chevalier‘s “Sweepin’ the Clouds Away” — but history’s clearly on the march.

Some lyrics — from Ella Fitzgerald‘s “Manhattan,” Patti Page‘s “Old Cape Cod,” Simon & Garfunkel‘s “Bleecker Street” — help set a sense of place; others — from “16 Going on 17” from Sound of Music,The Crystals‘ “He Hit Me (It Felt Like a Kiss),” Nashville Teens‘ “Tobacco Road” — get specific about the action at hand. And while fuzzily remembered No. 1 pop songs from the Tornadoes, Kyu Sakamoto, Paul Mauriat and Jeannie C. Riley have shown up, more common are deep album tracks that were never hits, from Santo & Johnny and Sergio Mendes to The Zombies and Mitch Ryder. LPs, especially in the pre-Beatles era, were for grownups with sophisticated hi-fis centerpiecing their midcentury modern decor, not greasy kid stuff like rock ‘n’ roll 45s. But rock grew up too. This mix, like Mad Men itself, proves what difference a decade can make. — Chuck Eddy