Timeless is a double album which includes moments from Streisand's New Year's Eve, 1999 and New Year's Day, 2000 shows at the MGM Grand Garden Arena on the Las Vegas Strip, which were part of her Timeless concert tour. The release is set up like a play in two acts and even has a two-minute entr'acte featuring conductor, Marvin Hamlisch, who is also present throughout the performance. It opens with a dramatization of her first, amateur recording session, in which Lauren Frost plays a part described in the credits as "Young Girl" though Streisand later refers to her as "my little-girl self" and "mini me". The rest of Act One traces Streisand's career from her club days to Broadway and her movie performances.

My Name Is Barbra, Two… is the second of two studio album tie-ins to Barbra Streisand's debut television special, My Name Is Barbra, which first aired on April 28, 1965. The Medley (Track 11) is the only music from the show, and the other tracks newly recorded for the album. Barbra remembers in Just For The Record: "'Second Hand Rose' became part of a tongue-in-cheek fantasy sequence which was shot at Bergdorf Goodman's…And thanks to people I loved and loved working with—Joe Layton, Dwight Hemion, Peter Matz, Robert Emmett, Tom John, and, of course, Marty—I was able to realize my dream." The album was also certified Platinum and peaked at #2 on the US charts and #6 in the UK charts.

Recorded in November 1962, this album marks the first official release of the legendary Greenwich Village Nightclub shows and includes 24 newly mixed performances from the original master tapes in Barbra’s personal collection. With the release of this album, Columbia Records celebrates 60 years of making records with Barbra Streisand, the artist with the longest continuous catalog on the label and the only artist - male or female - on any label to chart #1 albums in every decade since the 1960s.