The album consists of live recordings from his sold-out June 14–15, 2006, tribute concerts at Carnegie Hall to the American actress and singer Judy Garland.

[1] Backed by a 36-piece orchestra conducted by Stephen Oremus, Wainwright recreated Garland's April 23, 1961, concert, often considered "the greatest night in show business history".

According to Pitchfork, Wainwright "started listening to the Carnegie Hall album in the weeks and months after September 11, craving some cheap showbiz cheer, but wound up discovering something deeper".

[10] Soon afterwards, he took the idea to New York-based theatrical producer Jared Geller (who would later co-produce the tribute concert with David Foster), hoping to turn a dream into a reality.

Eventually, Geller agreed to assist with the production and the two found space in Wainwright's schedule to book Carnegie Hall a year in advance.

[18] Part of the success of the tribute concerts can be attributed to the amount of press attention received and the eagerness of other artists to participate in the event.

[24] To promote the album, Wainwright's website linked to an online store where fans could purchase merchandise, including several shirt designs, concert posters, programs and other collectibles.

Celebrities attending the Carnegie Hall shows included Justin Bond ("Kiki" of Kiki and Herb), Patricia Field, Gina Gershon, Joel Grey, Marc Jacobs, Michael Kors, Tony Kushner, Ann Magnuson, Sarah Jessica Parker, Kate Pierson, Fred Schneider, the Proenza Schouler boys, Chloë Sevigny, John Waters and Viktor & Rolf.

[27][28] Famous faces turned out at the concerts in Europe as well, including Julian Barratt, Keane frontman Tom Chaplin, Julia Davis, David Furnish, Mark Gatiss, Richard E. Grant, Jeremy Irons, Lulu, Paul Morley, Siân Phillips, Imogen Stubbs and Teddy Thompson.

Celebrities at the Hollywood Bowl show included Jamie Lee Curtis, Jimmy Fallon, Jake Gyllenhaal, Debbie Reynolds and Rod Stewart.

[30] "Hail[ing] from a golden era dotted with trolley cars, Cadillacs, and glitzy jazz clubs",[1] the set list included more than 25 American swing tunes, jazz and pop standards, including two Rodgers and Hart classics ("This Can't Be Love", "You're Nearer"), three from brothers George and Ira Gershwin ("Who Cares?

[14] Some of the well-known arrangements by orchestrators like Nelson Riddle and Conrad Salinger had to be reconstructed, since their music charts were not available, and most of the songs had to be transposed, since Wainwright was performing them in a different key.

Time magazine, in reviewing Garland's 1967 Palace Theatre engagement, disparagingly noted that a "disproportionate part of her nightly claque seems to be homosexual".

[33] A connection is frequently drawn between the timing of Garland's death and funeral, in June 1969, and the Stonewall riots, the flashpoint of the modern Gay Liberation movement.

[11][35] Wainwright also claims his mother (Canadian folk musician Kate McGarrigle) forced him to perform "Over the Rainbow" for guests while growing up, a song he often included in his concert repertoire as an adult.

[9] In his review for Rolling Stone, Robert Christgau stated it was "a relief to hear him essay the show tunes and Tin Pan Alley chestnuts of this tribute album".

[43] Dave Hughes of Slant Magazine had positive comments about the album: "That Wainwright has the temerity to cover such a bona fide classic—and the chops to pull it off without breaking a limb or his brain—speaks both to his ambition and to his prodigious abilities.

[43] Entertainment Weekly's Chris Willman wrote that Wainwright's "delicate upper range is nicely attuned to some of the ballads, but anything that requires belting is pretty much a loss".

[45] Dave Hughes' review pointed out Wainwright's "problem with the brassy high notes in an otherwise energetic take on 'That's Entertainment'", but admits it would be unfair to hold this against him since Garland's live performance was not perfect either.