Frank & Don.

Frank Sinatra released "In the Wee Small Hours" in 1955. The LP marked Sinatra's foray into the concept album, and it is characterized by a "mood of late-night isolation and aching lost love".

Sinatra's 1955 album inspired the title of a Season Three episode of AMC's hit drama Mad Men. "Wee Small Hours" is set in September of 1963 and the episode first ran in 2009--8 and 54 years after the release of the album, respectively. Despite the passage of time, Sinatra's album remains relevant to set the tone of the television episode.

Mad Men chronicles the work and womanizing of Don Draper, creative director at New York firm Sterling Cooper. "Wee Small Hours" begins just then with an early morning phone call for Don from client Conrad Hilton. Don leaves his wife Betty and their new baby, presumably to go to work, but on his way to the office, Don sees his daughter's primary school teacher jogging. He picks her up in his car and tries to pick her up for "coffee", but she resists his advances. Don never plays the jilted lover--he always gets the girl (and eventually succeeds with the teacher), but so far, Sinatra's "In the Wee Small Hours" fits the mood of this episode.

Other characters have their own "Wee Small Hours" moments as well. Betty begins her relationship with politician Henry Francis; (spoiler!) they marry after Betty divorces Don at the end of the season. At Sterling Cooper, a client comes on to Sal, the closeted art director. Jilted and embarrassed, the client calls the agency and demands that Sal be fired for being "uncooperative".

By the end of the episode, Sal has called his wife to tell her he loves her, Betty and Henry have shared their first kiss, and Don has slept with the teacher. The episode ends at night, just as it began. Much of the action that transpires in "Wee Small Hours" follows the "late-night longing" theme of Sinatra's album.

In characteristic Mad Men style, the only musical soundtrack to the show is the song that plays just after the last scene and through the credits. Despite the title of the episode, Sinatra does not make a musical appearance in this final song. The writers of Mad Men create a very particular and subtle mood for the episode by naming it after Sinatra's album but not invoking Sinatra's music.

(This link will take you to a John Mayer cover of  "In the Wee Small Hours of the Morning."  It's also relevant, considering that Don Draper and John Mayer share a talent for making women swoon and for treating ladies with complete disrespect.)