2000s
John Hammond's Wicked Grin, a collection of Waits cover songs, was released in 2001. Waits appears on most songs, playing guitar, piano, and/or offering backing vocals. The album also includes the traditional hymn "I Know I've Been Changed", performed as a duet by Hammond and Waits.
Tori Amos included a cover of the song "Time", from Rain Dogs on her 2001 album Strange Little Girls.
In 2002, Waits simultaneously released two albums, Alice and Blood Money. Both collections had been written almost 10 years previously and were based on theatrical collaborations with Robert Wilson; the former a musical play about Lewis Carroll, and the latter an interpretation of Georg Büchner's play fragment Woyzeck. Both albums revisit the tango, Tin Pan Alley, and spoken-word influences of Swordfishtrombones, while the lyrics are both profoundly cynical and melancholic, exemplified by "Misery is the River of the World" and "Everything Goes to Hell." "Diamond in Your Mind", which Waits wrote for Wilson's Woyzeck, did not appear on Blood Money; however, it did emerge on Solomon Burke's album Don't Give Up on Me of the same year. While Waits has played the song live a number of times, an official version would not be released until 2007. The same year, Waits contributed a version of "The Return of Jackie and Judy" by The Ramones to the compilation album We're a Happy Family: A Tribute to Ramones, which was released in 2003 on Columbia Records. That same year, Waits was also a judge for the 2nd annual Independent Music Awards to support independent artists' careers. Waits was also a judge for the 10th annual Independent Music Awards.
Waits released Real Gone, his first nontheatrical studio album since Mule Variations, in 2004. It is Waits's only album to date to feature absolutely no piano on any of its tracks. Waits beatboxes on the opening track, "Top of the Hill", and most of the album's songs begin with Waits's "vocal percussion" improvisations. It is also more rock-oriented, with less blues influence than he has previously demonstrated. The same year, Waits contributed backing vocals to the track "Go Tell It on the Mountain" on the Grammy Award (Best Traditional Gospel Album)-winning album of the same name by The Blind Boys of Alabama. He also contributed a version of Daniel Johnston's "King Kong" to the tribute album The Late Great Daniel Johnston: Discovered Covered, released on Gammon Records.
At this time, Waits made a return to acting after a five-year break, marked at first by the re-release of his 1993 Jim Jarmusch-directed short Coffee and Cigarettes: Somewhere in California, costarring Iggy Pop, compiled in Coffee and Cigarettes. In 2005, Waits appeared in the Tony Scott film Domino as a soothsayer. In the same year, Waits appeared as himself in Roberto Benigni's romantic comedy La Tigre e la Neve, set in occupied Baghdad during the Iraq War. In the movie, Waits appears in a dream scene as himself, singing the ballad "You Can Never Hold Back Spring" and accompanying himself at the piano.
A 54-song three-disc box set of rarities, unreleased tracks, and brand-new compositions called Orphans: Brawlers, Bawlers & Bastards was released in November 2006. The three discs are subdivided relating to their content: "Brawlers" features Waits's more upbeat rock and blues songs; "Bawlers", his ballads and love songs; and "Bastards", songs that fit in neither category, including a number of spoken-word tracks. A video for the song "Lie to Me" was produced as a promotion for the collection. Orphans also continues Waits's newfound interest in politics with "Road to Peace", a song about the Israeli–Palestinian conflict. The album is also notable for containing a number of covers of songs by other artists, including The Ramones ("The Return of Jackie and Judy" and "Danny Says"), Daniel Johnston ("King Kong"), Kurt Weill and Bertolt Brecht ("What Keeps Mankind Alive"), and Leadbelly ("Ain't Goin' Down to the Well" and "Goodnight Irene"), as well as renditions of works by poets and authors admired by Waits, such as Charles Bukowski and Jack Kerouac and a previously released duet with Mark Linkous of Sparklehorse entitled "Dog Door". Waits' albums Orphans: Brawlers, Bawlers & Bastards and Alice are both included in metacritic.com's list of the "Top 200: Best-Reviewed Albums" since 2000 at #10 and #20, respectively (as of November 2009). The same years, Waits appeared on Sparklehorse's album Dreamt for Light Years in the Belly of a Mountain, playing piano on the track "Morning Hollow."
Five different versions of Waits's song "Way Down in the Hole" have been used as the opening theme songs for the HBO television show The Wire. Waits's own version, from Frank's Wild Years, was used for season two. The other versions used for the series were performed by, in season order, The Blind Boys of Alabama, The Neville Brothers, "DoMaJe" and Steve Earle.
Waits made a number of high-profile television and concert appearances between 2006 and 2010. In November 2006, Waits appeared on The Daily Show and performed "The Day After Tomorrow." This was significant for his having been only the third performing guest on the show, the first being Tenacious D and the second The White Stripes. On May 4, 2007, Waits performed "Lucinda" and "Ain't Goin' Down to the Well" from Orphans on the last show of a week Late Night with Conan O'Brien spent in San Francisco. There was a short interview after the last performance. Waits also played in the Bridge School Benefit on October 27–28, 2007 with Kronos Quartet.
On July 10, 2007, Waits released the download-only digital single "Diamond In Your Mind". The version of the song was recorded with Kronos Quartet, with Greg Cohen, Philip Glass, and The Dalai Lama at the benefit concert "Healing The Divide: A Concert for Peace and Reconciliation" at Avery Fisher Hall, recorded on September 21, 2003.
Waits's song "Trampled Rose" (from Real Gone) appeared on the critically acclaimed album Raising Sand, a collaboration between Robert Plant and Alison Krauss. Waits also provided guest vocals on the song "Pray" by fellow ANTI- artists The Book of Knots on their album Traineater.
He played the role of Kneller in the film Wristcutters: A Love Story, which opened in November 2007.
On January 22, 2008, Waits made a rare live appearance in Los Angeles, performing at a benefit for Bet Tzedek Legal Services—The House of Justice, a nonprofit poverty law center.
On May 7, 2008, Waits announced the Glitter and Doom Tour starting in June 2008, touring cities in the southern United States and subsequently announced a series of dates in the UK, Ireland and mainland Europe. Waits was awarded the key to the city of El Paso, Texas during a concert on June 20, 2008. In his generally positive review of the opening show of the tour, The Wall Street Journal critic Jim Fusilli described Waits' music thus:
The 58-year-old Mr. Waits ... has composed a body of work that's at least comparable to any songwriter's in pop today. A keen, sensitive and sympathetic chronicler of the adrift and downtrodden, Mr. Waits creates three-dimensional characters who, even in their confusion and despair, are capable of insight and startling points of view. Their stories are accompanied by music that's unlike any other in pop history.On May 20, 2008, Scarlett Johansson's debut album, entitled Anywhere I Lay My Head, featured covers of ten Tom Waits songs. Waits made an appearance on the album The Spirit of Apollo by alternative hip hop project N.A.S.A., on the track "Spacious Thoughts."
Waits wrote the following introduction for the Tompkins Square compilation People Take Warning – Murder Ballads & Disaster Songs, 1913–1938:
In the late 1920's and early 1930's, the Depression gripped the Nation. It was a time when songs were tools for living. A whole community would turn out to mourn the loss of a member and to sow their songs like seeds. This collection is a wild garden grown from those seeds.In late 2009, Terry Gilliam's film The Imaginarium of Doctor Parnassus was released, with Waits in the role of Mr. Nick. Production began in December 2007 in London. Star Heath Ledger's death in January 2008 cast doubt on the film's future, but the production was salvaged with the addition of new actors playing his character in scenes he did not complete.
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