Amy Winehouse, “You Know I’m No Good”

As they promised to show us what it was like to live, work and play in 1960 New York, AMC chose a more modern theme for its very first trailer.

Jan and Dean, “Sidewalk Surfing”

Another fun party song, no matter the theme, and part of another Draper road trip to California.

The Pentagons, “To Be Loved”

Season three unearthed this doo-wop gem. Thematically, it’s what everyone on this show wants – and then tries very hard to screw up.

Etta James, “Trust In Me”

A song that not only reminds us who we’ve lost in 2012, but echoes the themes of a series where even some of your favorite people are usually not very trustworthy.

Sonny and Cher, “I Got You, Babe”

When we left Don Draper in season four, he’d surprised us all by proposing to his French bombshell of a secretary, Megan, and this song was playing.

–Mary Dixon & Zack Nechvatal, CBS Radio Chicago; Jillian Mapes, CBS Local