"Dream a Little Dream of Me" was recorded for the Mamas & the Papas April 1968 album release The Papas & The Mamas. The group had often sung the song for fun, having been familiarized with it by member Michelle Phillips, whose father had been friends with the song's co-writer, Fabian Andre, in Mexico City where Michelle Phillips' family had resided when she was a young girl. "Mama" Cass Elliot suggested to group leader John Phillips that the group record "Dream a Little Dream of Me". According to him she was unhappy while recording the song, objecting to its campiness. However, Elliot herself would later tell Melody Maker: "I tried to sing it like it was 1943 and somebody had just come in and said, 'Here's a new song.' I tried to sing it as if it were the first time."
In the album version, recorded with the Mamas and the Papas, a spoken introduction from an engineer is heard mentioning a drink, and then concluding with the words: "And now introducing: Mama Cass". Only the last part was heard on the single version of the song. Cass did her own whistling, which is heard before the song's fade.
By the time of the album's release, there were strong indications that the Mamas & the Papas were set to disband, a perception strengthened by the failure of the lead single "Safe in My Garden". Having an opportunity to promote the group's best-known member as a soloist, Dunhill Records gave a June 1968 single release to the "Dream a Little Dream of Me" track with the credit reading - to John Phillips' displeasure - "Mama Cass with the Mamas & the Papas"; in its UK release the artist credit simply read "Mama Cass". Promoted in the US press and on billboards with a photograph of a discreetly but obviously nude Elliot lying in a bed of daisies, "Dream a Little Dream of Me" peaked at #12 on the Billboard Hot 100 that August (its Cash Box peak was #10 and in Record World it reached #8). The BillboardEasy Listening chart ranked the single as high as #2. In the UK "Dream a Little Dream of Me" reached #11 that September; the track also afforded Mama Cass a hit in Ireland (#13) and South Africa (#8). In Australia the Go-Set Top 40 chart ranked "Dream a Little Dream of Me" at #1 for the weeks of 4 & 11 September 1968. "Dream a Little Dream" was released as a single in Europe in 1992 - credited to the Mamas and the Papas and featuring that group's #1 hit "Monday, Monday" as the B-side - to reach #5 in Germany and #22 in Switzerland. In Australia the song spent two weeks at #1, and was the 16th biggest hit of 1968.
A slightly different version of "Dream a Little Dream of Me" was included on Elliot's solo debut album, Dream a Little Dream.
The release of the Mama Cass single of "Dream a Little Dream of Me" prompted a cover by Anita Harris which was recorded at Olympic Studios in a session produced by Mike Margolis with Alan Tew as musical director. Released 26 July 1968, the Harris version debuted in the UK Top 50 dated 10 August 1968 at #46 ahead of the Cass version at #49 although the latter would vault into the Top 30 and then Top 20 over the next two weeks while the Harris version would never reach the Top 30. However Harris's version of "Dream a Little Dream of Me" would maintain a lower chart presence throughout the ascendancy of the Cass version with Harris's single peaking at #33 the week after Cass's peak at #11. Both Cass's and Harris's versions of the song have an inaccurate rendering of the middle eight bars.
English singer-songwriter Robbie Williams recorded "Dream a Little Dream of Me" (retitled "Dream a Little Dream") for his tenth studio and second swing album, Swings Both Ways (2013). While the album version is a duet with Lily Allen, she was omitted from the single version, which was released on 13 December 2013 as the album's second single.
Pete Doherty and Carl Barat performed it as a party piece during the first iteration of The Libertines. Most recently they performed it at the Hackney Empire on April 12, 2007, during a surprise reunion show for the duo. Barat often tap-dances during the performance.