10 Standout Collaborations From Eric Clapton’s Crossroads Guitar Festival

By Ming Lee Newcomb Mar 31, 2019 8:30 am PDT

Earlier in the week, Eric Clapton announced the return of his long-running Crossroads Guitar Festival. Scheduled for American Airlines Center in Dallas on September 20 – 21, the famed guitarist has tapped a number of high-profile collaborators to join him for the two-day event, including Derek Trucks, Jeff Beck, Susan Tedeschi, Bonnie Raitt, Gary Clark Jr., Joe Walsh, Peter Frampton, Jimmie Vaughan, Robert Randolph, Sheryl Crow, Billy Gibbons, Buddy Guy Band, Doyle Bramhall II, Los Lobos, Keb Mo, Tom Misch and many others.

Clapton’s Crossroads Guitar Festival was officially established in 2004, though he previewed the format in 1999 with an all-star show at Madison Square Garden. In the years since, the famed Cream guitarist has hosted the concert series five times as a benefit for his drug treatment center in Antigua, Crossroads Centre. Each showcase has found Clapton curating a stellar lineup of musicians, offering the chance to see multiple generations of music legends collaborate with one another. We’ve compiled 10 highlights from past editions — two from each year — below.

Sheryl Crow & Eric Clapton – “My Favorite Mistake” (1999)

On June 30, 1999, at the iconic Madison Square Garden, Clapton hosted his first-ever benefit for the Crossroads Centre. While the three-hour event was not technically branded under the banner of the Crossroads Guitar Festival, the evening — which was promoted as Eric Clapton & Friends in Concert — set the stage for the series. During the performance, Clapton called upon Sheryl Crow to join him, with the “All I Wanna Do” singer going on to perform at subsequent editions of the festival.

During the show, Crow and Clapton performed a number of songs together, including her own “The Difficult Kind” and a cover of Jimi Hendrix’s “Little Wing.” The show also saw the duo team up on a rendition of “My Favorite Mistake,” which Crow allegedly wrote about her brief romance with the “Layla” songwriter in the late ’90s. You can watch the performance, which was later broadcast on VH1 and released on DVD, below, courtesy of uploader Lucas Guru:


Bob Dylan & Eric Clapton – “Crossroads” (1999)

During that first 1999 showcase at Madison Square Garden, Clapton was joined by a number of other high-profile artists, including R&B singer Mary J. Blige, jazz saxophonist David Sanborn and a handful of frequent collaborators and studio musicians, who served as the evening’s backing band. Toward the end of the show, legendary singer-songwriter Bob Dylan joined the festival host for his own “Don’t Think Twice, It’s Alright,” which appeared on 1963’s The Freewheelin’ Bob Dylan.

The duo then drew from Cream’s traditional catalog, performing their fan-favorite cover of Robert Johnson’s “Cross Roads Blues,” which the British rock trio re-popularized in the late ’60s under the name “Crossroads.” With Dylan and Clapton sharing a microphone, the pair worked through a lively take on the blues standard. The song — which ended with a brief but spirited solo from Clapton — marked an end to Dylan’s sit-in. You can watch the collaboration for yourself below, courtesy of uploader rylock22:

Eric Clapton & Friends – “I Shot The Sheriff” (2004)

In 2004, Clapton debuted his first official Crossroads Guitar Festival at Dallas, Texas’ Cotton Bowl stadium. The event spanned from June 4 to June 6, with the final day of the festival featuring a special showing by Clapton and his band along with special guest Jeff Beck. After 20 performances ranging in length across the day, the super jam fell toward the end of the show ahead of ZZ Top‘s final eight songs of the night. Performing 12 cuts, the lineup, which also featured Doyle Bramhall II among others, performed a selection of covers and Cream and Clapton originals.

Midway through the set, the group, sans Beck, offered a powerful eight-minute rendition of Bob Marley’s “I Shot The Sheriff.” With a tight backing vocal section of Sharon White and Michelle John, Clapton’s vocal prowess was on display, captivating the crowd with his emotive style. Notably, the end of the song featured an extended improvisation, with a buoyant, blues-laced jam that bordered on transcendent as Clapton riffed on the upper ranges of his guitar. Listen to the cover below, courtesy of uploader Ioannis Vatistas:

JJ Cale & Eric Clapton – “After Midnight > Call Me The Breeze” (2004)

During the 2004 edition of Crossroads Guitar Festival, Clapton was a constant presence throughout the weekend. In addition to his own sets, the guitarist was regularly seen on the side stage during others’ performances, appreciating the lineup he had curated and occasionally sitting in throughout the day. During JJ Cale‘s daytime set, Clapton served as a special guest for its entirety, giving the nod to the pioneering songwriter.

Clapton’s appreciation for Cale is longstanding. In addition to his immensely popular covers of Cale’s “Cocaine” and “After Midnight,” the former Yardbirds member has spoken openly about his love of the iconic musician, declaring in his 2007 biography that Cale was “one of the most important artists in the history of rock, quietly representing the greatest asset his country has ever had.” Watch the duo perform Cale’s “After Midnight” and “Call Me The Breeze” below, courtesy of uploader ANDRHE FAME:

Steve Winwood & Eric Clapton – “Presence Of The Lord > Dear Mr. Fantasy” (2007)

In 2007, Clapton once again revived his Crossroad Guitar Festival, this time bringing the series to Bridgeview, Illinois’ Toyota Park on July 28. The event, which had a capacity of 28,000 patrons, sold out in less than half an hour, with the show boasting a lineup of Clapton alongside artists like Robert Randolph and John Mayer among many others. During the show, Clapton hosted his own solo set, which saw the famed performer joined by The Band’s Robbie Robertson and Traffic’s Steve Winwood.

During Winwood’s appearance, the duo performed a number of tunes together, drawing on the catalog of Blind Faith, their 1969 supergroup also featuring Ginger Baker and Ric Grech. In addition to cuts like “Can’t Find My Way Home” and “Had To Cry Today,” the band offered takes on “Presence of the Lord” and Traffic’s “Dear Mr. Fantasy.” Watch both songs below, courtesy of uploader acdcrockno1:

Derek Trucks & Eric Clapton – “Little Queen of Spades” (2007)

During the 2007 showcase, Clapton also welcomed guitarist Derek Trucks into the fold. Trucks was on hand to perform the festival with his own Derek Trucks Band, with powerhouse vocalist Susan Tedeschi guesting for their performance and hinting at the formation of Tedeschi Trucks Band, which would come together a few years later in 2010. While in Illinois, Trucks was invited out during Clapton’s solo set with his band, offering takes on classics such as Derek and the Dominos’ “Tell The Truth.”

Later during the show, the young prodigy and Allman Brother Band protege guested with Clapton during a version of “Little Queen of Spades,” a Robert Johnson blues tune from the first half of the 20th century. After the 12-minute rendition’s opening verses, Trucks had time to unleash on the slide guitar with an explosive solo. Watch the blistering cover below, courtesy of Ray Stevie:


B.B. King & Eric Clapton – “Thrill Is Gone” (2010)

In 2010, the Crossroads Guitar Festival once again returned to Bridgeview, Illinois’ Toyota Park, marking the third official edition of the event. With Bill Murray serving as the MC of the festival (his introduction can be watched here), Crossroads grew in stature, drawing even larger buzz with a lineup featuring Sonny Landreth, John Mayer Trio, Buddy Guy, Doyle Bramhall II and others. Notably, the show also hosted the late and great guitarist B.B. King, who teamed with Clapton for a rendition of his hit cover of Roy Hawkins and Rick Darnell’s 1951 blues standard “Thrill Is Gone.”

With both all-star musicians seated on stage, the song highlighted two of the greatest guitarists of the 20th century. With the cover spanning almost 12 minutes, the track offered plenty of room for both musicians, as well as the house band, to improvise and expand. Throughout the number, the band offered a thrilling and soulful performance, which can be watched below, courtesy of NEA ZIXNH:


Sheryl Crow, Vince Gill, Albert Lee & Eric Clapton – “Tulsa Time” (2010)

Collaborations abounded throughout the 2010 edition of Crossroads Guitar Festival, both during Eric Clapton’s own solo sets and other artists’ shows across the day. One highlight of the event, which took place on June 26, was the Sheryl Crow-led take on “Tulsa Time,” a popular country tune written by Danny Flowers and first recorded by Don Williams.

However, “Tulsa Time” was also recorded by Clapton on his 1978 record Backless, and appropriately, the guitarist sat in for the tune, along with country stars Albert Lee and Vince Gill. During the jubilant rendition, the group gracefully worked through the cover, with each Gill, Lee and Clapton each given their moment to stretch out and solo. Listen to six-minute performance below, courtesy of Kurt Wells:

The Allman Brothers Band & Eric Clapton – “Why Has Love Got To Be So Sad” (2013)

In 2013, the Crossroads Guitar Festival left its previous home outside Chicago, returning to Madison Square Garden on April 12 and 13. During the weekend, the Allman Brothers Band performed a headlining set, which made up for their originally scheduled 2010 appearance. Across the festival, the iconic southern rock act offered many of their classic numbers during their standalone showcase, while frontman Gregg Allman went onto perform on the final day during a super jam with Clapton and ABB guitarist Warren Haynes.

Predictably, Eric Clapton jumped at the chance to sit-in with the rock legends, offering his renowned guitar stylings on “Why Has Love Got To Be So Sad,” off Derek and the Dominos’ 1970 release Layla and Other Assorted Love Songs. The near 9-minute take opened with a drum solo from ABB’s percussion section of Butch Trucks and Jaimoe, with Clapton taking on the vocal duties for the track. The propulsive tune was highlighted by the explosive interplay between Derek Trucks, Haynes and Clapton, and complemented by Allman’s additions on the keys and Otiel Burbridge‘s locked-in performance on bass. Watch the all-star rendition below, courtesy of Eric Clapton:

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Keith Richards & Eric Clapton – “Key To The Highway” (2013)

The 2013 lineup for the Crossroads Guitar Festival boasted one of the strongest lineup in its history, with a number of familiar faces (such as B.B. King, John Mayer, Jeff Beck, Robert Randolph and others) returning for the show, in addition to a handful of high-profile new artists. For example, famed Rolling Stones co-founder Keith Richards made his debut at the series, guesting with Eric Clapton on a cover of the blues standard “Key To The Highway.”

With the two classic-rock legends on stage, the audience and the musicians themselves delighted in the all-star collaboration, with the mutual admiration propelling the standout moment on the final day of the weekend. Richards primarily led the tune, offering his characteristic vocals to the song, while Clapton took on the brunt of the guitar soloing. Watch the cover below, courtesy of Front Row Dave:

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