News of the song's future release was first published on the official Eminem site on April 30, 2009, as a part of the official countdown. The song features, and is also produced by Dr. Dre. It is one of the only two songs on the album to have guest appearances; the other song, "Crack a Bottle", also features Dr. Dre, as well as 50 Cent. The song leaked on May 4, one day before its official release. The single has no video. The song has a drug related theme similar to most of the songs in the album.
The song has been well received by fans and critics alike, MTV summarized "Old Time's Sake" as "featuring a party vibe". The article went on to describe that "the record has the familiar West Coast bounce, and that Dr. Dre himself lead the song with a "simple sing-songy flow" as well as adult content." Allmusic highlighted the song. The Guardian was negative: "More troubling is the sense of going through the motions - something that comes with the album's attempts to scandalise, and which seems to have seeped through into the song title" Louis Pattison was also negative: "‘Old Time’s Sake’ with Dre heralds a mid-album slump." Pitchfork was really positive: "the mere fact he's working with Dr. Dre is seen as cause for celebration (the entirety of "Old Time's Sake" is great)." Rolling Stone described "there's "Old Time's Sake," where Dre drops tasteless lines about getting Em stoned again."