In 1965, the brash 23-year-old concert promoter, stage manager and budding talent scout Joe Boyd took up his new job in Elektra Records’ London office. Charged with raising the profiles of Judy Collins, Phil Ochs, Tom Rush and other Elektra folk acts, Boyd also focused on creating a follow-up to the hit Elektra compilation The Blues Project, which staffer Paul A. Rothchild and label head Jac Holzman had put together by culling the best talent primarily from New York’s Greenwich Village and Boston’s blues-obsessed scene.

With a little help from Manfred Mann singer Paul Jones, Boyd succeeded in gathering British musicians, recording three tracks in London, eventually released on the compilation What’s Shakin’. The ad-hoc group dubbed Powerhouse featured guitarist Eric Clapton, drummer Pete York, bassist Jack Bruce, Ben Palmer on piano, Jones on harmonica and the teenage sensation Steve Winwood (credited as Steve Anglo) as lead vocalist.

Clapton was already highly impressed by the 15-year-old Winwood, a Hammond organ virtuoso who could successfully tackle material like Ray Charles’ “Georgia on My Mind,” which other British vocalists found intimidating. Even as Clapton formed Cream with Bruce and Ginger Baker, finding worldwide fame, and Winwood achieved success with the Spencer Davis Group and Traffic, they kept in touch, waiting for the right moment to collaborate again.

The short-lived “supergroup” Blind Faith provided the opportunity for the two friends to work jointly, but they only produced one (classic) LP and a series of hit-and-miss live performances before imploding in 1969 after less than a year. As Clapton later confessed, given his musical and personal bond with Winwood, “me leaving, or dissolving, pulling out of Blind Faith, was an act of infidelity, in a way.”

The chance to write some new history finally re-appeared in 2007, when Winwood guested with Clapton’s band during his annual Crossroads Guitar Festival charity concerts. In a seven-song set, they played three Blind Faith tunes and the Powerhouse arrangement of Robert Johnson’s “Cross Road Blues.” Clapton was energized and proposed doing a few shows based on a playful and unorthodox principle: they would each choose which songs from the other man’s catalog to include in the set. For instance, this meant Winwood insisted Clapton perform “Forever Man,” which Winwood thought he’d been neglecting, leading to one of the best live renderings in Clapton’s discography.

By the time the three sold-out shows rolled around, February 25, 26 and 28, 2008, at Madison Square Garden, it had been decided to film and record the concerts for release on DVD and CD through Clapton’s label Reprise. Twenty-one songs made the final cut, including four from Winwood’s time with Traffic, four Blind Faith tunes, a two-song tribute to Jimi Hendrix, several lesser-known blues, and picks from their solo careers.

In support, three musicians who’d played with both men in concert and in studios were drafted: bassist Willie Weeks, drummer Ian Thomas and keyboardist Chris Stainton. Their solid backing gives Winwood and Clapton exceptional space to stretch out.

Winwood had been confident in the spotlight since his teenage years, but Clapton went through much of his career concentrating on guitar and denigrating his singing. Speaking about his first recorded vocal on 1966’s “Rambling on My Mind,” cut when he was playing with the Blues Breakers, Clapton recalled, “John Mayall insisted I do vocals. This was much against my better judgment, since most of the guys I longed to emulate were older and had deep voices, and I felt extremely uncomfortable singing in my high-pitched whine.” Yes, the man who produced huge hits singing “I Shot the Sheriff,” “After Midnight,” “Tears In Heaven,” “Wonderful Tonight,” etc., was once so shy he could barely take the microphone.

Clapton had completed his long journey from reluctant vocalist and team-player to bandleader and expressive singer, but having the super-talented Winwood on board allowed him to re-arrange the balance of some of his material for the Madison Square Garden dates. Winwood, for instance, sings the Cream arrangement of “Crossroads,” and for the first time the two men share vocals on “Presence of the Lord.” Clapton had written it just before Blind Faith came together, but despite its personal and sensitive nature had drafted Winwood to deliver the lyrics.

With veteran keyboardist Stainton in the band, it was also possible to give Winwood plenty of room for his outstanding guitar playing, in addition to many jaw-dropping Hammond organ solos. For the opening “Had to Cry Today” and concluding “Dear Mr. Fantasy” especially, the sparring on guitar is transcendently robust. When Winwood delivers the concert’s first line, “It’s already written that today will be one to remember,” one can immediately feel this is going to be a unique show.

In a performance of nearly two-and-a-half hours, there are too many highlights to describe fully here, but certainly Clapton’s second long solo during “Forever Man,” the powerful vocal and Hammond solo on “Georgia on My Mind,” and the interplay between Stainton’s organ and Winwood’s barrelhouse piano on “Sleeping In the Ground,” originally cut by Sam Meyers for Chess in 1956, must be mentioned. Blind Faith played that last one during their debut concert in Hyde Park, but they didn’t include it on the Blind Faith LP. Quite an interesting choice for the setlist, especially with Winwood insisting they include “Rambling on My Mind” too.

In an interview on the DVD, Clapton describes the performance of Jimi Hendrix’s “Voodoo Chile” as “like stepping off a cliff.” Winwood had appeared on the original Electric Ladyland version, but here takes the lead vocal: “On the night I was born/I swear the moon turned a fire red.” The lengthy performance is breathtaking, with Winwood and Clapton bringing their own personalities to the playing, without any attempt to imitate Hendrix (if that were even possible).

After hearing Hendrix for the first time, jamming with Cream in a small club, Clapton was smitten: “He played just about every style you could think of, and not in a flashy way. He did a few of his tricks, like playing with his teeth and behind his back, but it wasn’t in an upstaging sense at all, and that was it. He walked off, and my life was never the same again.”

Clapton had been performing Hendrix’s melancholy “Little Wing” since he cut it with Derek and the Dominos for Layla and Other Love Songs in 1970, and the performance that proceeds “Voodoo Chile” is focused and passionate. (It’s interesting that the duo did not choose “Layla” for the setlist, but grabbed “Little Wing.”)

“Double Trouble,” which Otis Rush recorded for the Cobra label in 1958, had a couple of high-profile performances in the Clapton tour log, including a great version recorded for The Old Grey Whistle Test television show in 1977, and a Rush-Clapton special at Montreux in 1986. It blazes here too.

“Split Decision” from Winwood’s Back in the High Life album and the poignant Traffic tune “No Face, No Name, No Number” are wonderful choices. There’s only one song not previously associated with either leader, Buddy Miles’ “Them Changes,” which came into the set by mutual agreement, and provided a bittersweet moment when Clapton announced to the crowd that Miles had died just a day before, having heard on his deathbed the group was playing it during their run.

The sheer fun of the three-night stand, and plans to bolster the release of the DVD and CD release in spring 2009, led to the announcement of a 14-city U.S. tour to begin June 10, 2009, in East Rutherford, New Jersey, with a last show in Las Vegas July 27. The sell-out tour saw Abe Laboriel Jr. replacing Thomas as drummer; the critical notices and audience reactions were ecstatic. [The souvenir from MSG is available in the U.S. here, in Canada here and in the U.K. here.]

The tour is rightly seen as a highlight of both Winwood and Clapton’s live performances, although these are ongoing: Winwood toured on a double bill with John Fogerty in September 2026, and Clapton was also on the road, ending with the latest edition of his Crossroads Guitar Festival, in Austin, Texas.