The Saddest Jock Jams is the cold open for the Season Six episode, Honeymoon.
Synopsis
Jake Peralta gets his Jock Jams Cd to celebrate Raymond Holt's promotion, but is missing a key piece of information.
Video
Cultural Reference
Jock Jams were a series of cds from ESPN that were essentially playlists of popular sports anthems. There were 6 total volumes released from 1995-2001. The song Jake plays on his boombox and the one he was going to play at his wedding are from the original Jock Jams, Volume 1 released in 1995.
Soundtrack
Song playing on Jake's boom box
The song Jake was going to surprise Amy with as their first dance
Trivia
The Lonely Island made an SNL Digital Short for their song, Boombox, (below) from their 2009 album, Incredibad. It is a cautionary tale about how dangerous boomboxes can be, the song and video features Andy Samberg walking into rooms playing songs from a boombox in serious situations.