"Ramblin' Gamblin' Man" is a song written and performed by Bob Seger (as the Bob Seger System). The song was originally released as a single in October 1968, then as a track on the album of the same name in April 1969. The single fared well, reaching No. 17 on the national charts. The original studio version, released in mono, had been unavailable to the public until it was included on Seger's 2011 compilation album Ultimate Hits: Rock and Roll Never Forgets. It was Bob Seger's first top 20 hit.

The song follows a I-VII-IV-I progression, a typical 1960s chord progression. The melody plays over a basic rock drum beat and an unmistakable organ riff that carry throughout the song. Seger's friend Glenn Frey, who later founded the Eagles, played acoustic guitar and sang back-up vocals.

The Bob Seger System synched to this song on a 1960s TV show called Happenin', hosted by Paul Revere. The clip exists on YouTube. Seger continued playing the song in concert with many various bands long after the Bob Seger System disbanded. A live version of the song from an Orlando concert on May 13, 1973 exists on www.worj.com. This version features Seger's (apparently unreliable) "Borneo Band", with prominent female vocalist Shaun Murphy (then known as Stoney). Another live version appeared on the 1976 live album Live Bullet, this time with the Silver Bullet Band backing Seger. The song finally dropped off of Seger's set list in 1983, but returned 23 years later during Seger's 2006-07 Face The Promise tour.

Artists such as Gov't Mule, The Black Keys, Black Oak Arkansas, The Guess Who, and Bruce Springsteen have also covered this song in concert.

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