JAS June Experience headliner Sheryl Crow's 10 most memorable videos

Sheryl Crow is one of the artists headlining this year’s Jazz Aspen Snowmass June Experience taking place June 24-July 6, with tickets on sale February 12. In honor of her performance we thought we’d take a look back at her amazing career as well as some of her best music videos. Crow burst onto the music scene at a time when TV stations like MTV and VH1 were still playing videos, and she has some great ones. Here are Sheryl Crow’s 10 most memorable music videos.

“All I Wanna Do”

The song and subsequent video became Sheryl Crow’s breakout hit from her 1993 debut album Tuesday Night Music Club.  The album was named after the loose songwriting collective Crow was a part of with then boyfriend and composer Kevin Gilbert, among other L.A. musicians and writers.  Although Tuesday Night Music Club was Crow’s first solo success, she had previous success as a singer with more than a few notable acts.  She was a backup singer for Michael Jackson on his 1987-89 Bad World Tour and performed with Jackson on the song “I Just Can’t Stop Loving You.”  She also sang for megastars Stevie Wonder, Kenny Loggins, and Don Henley.  Crow has said that she lifted the lyrics for “All I Wanna Do” from an obscure poetry book she found in an L.A. used bookstore.  The video, like the song, is a delightful romp by Crow and band through some of the seedier sides of Los Angeles.

“Leaving Las Vegas"

The song was the second single off Music Club but was actually Crow’s first promotional video for the album. Fellow Tuesday Night Music Club member David Baerwald wrote the song and the video was directed by David Hogan who also shot the video for “All I Wanna Do.”  The video for “Leaving Las Vegas” features some noir style Chiaroscuro lighting of Crow playing her guitar in the dark, juxtaposed with classic Las Vegas imagery.


“Can’t Cry Anymore”

Another single from Music Club, which would go on to sell 7 million copies in the U.S. and U.K. in the 90s and also garnered Crow three Grammy awards.  The video shows Crow performing the song with band as well as what looks to be 8mm film of intimate band moments on the tour bus.  The video also features Crow playing an accordion, showcasing her multi-instrumental talent that she learned as a music major at the University of Missouri.

“If It Makes You Happy”

The first single from Crow’s self-titled second album, “If It Makes You Happy” was an instant radio success and netted the singer two more Grammys.  The video is also engaging, showing Crow as part of a museum display of endangered species, a nice bit of expressionism harkening to the song’s themes of feeling trapped and unsatisfied.

“Everyday Is A Winding Road”

The second single from Crow’s eponymous album was another success for the singer songwriter.  The song debuted at #11 on the Billboard Hot 100 and was nominated for a Grammy.  The video, filmed in sepia and directed by Peggy Sirota, is a symbolic look at the interconnectivity of all things as the film follows a toy airplane as it goes from life experience to life experience, once again echoing the theme of the song.

“A Change Would Do You Good”

Multiple versions for the music video were shot for the fourth single off Sheryl Crow.  One version, directed by Crow and Lance Acord, shows Crow singing and playing guitar in the street while another Crow throws her possessions out an unseen apartment window, culminating in throwing herself out the window.  The black and white cityscape along with medium and long shots of Crow are reminiscent of Bob Dylan’s video for “Subterranean Homesick Blues.”

Another version features Crow as a kind of Samantha character from Bewitched as she changes people lives with a wag of her finger.  The video also features notable cameos from Mary Lynn Rajskub, Heather Matarazzo, Jeff Garlin, Ellen DeGeneres, Molly Shannon, Andy Dick and Toby Huss.  While the black and white version is more artistic the “Bewitched” version is fun too.

“My Favorite Mistake”

Crow released The Globe Sessions in 1998 and the album’s debut single was “My Favorite Mistake.”  Rumors were flying at the time that Crow was involved with guitar god Eric Clapton and that the song was about him, although Crow played it coy on just who the song was about.  Crow has said that it is one of her favorite songs to play.  The video was directed by Samuel Bayer and uses sparse mise-en-scene and dimmed lighting, leaving the focus on Crow.  Another great artistic video, the whole shoot takes place on a practically empty set, with Crow sometimes dancing and sometimes banging against the walls, mirroring the bittersweet sounds and themes of the song.


“Steve McQueen”

The second single off her 2002 album C’mon C’mon, won Crow another Grammy for best Female Rock Performance.  Directed by Wayne Isham, the video is pretty cool, living up to its namesake.  It features Crow riding around in muscle cars, recreating various scenes from Steve McQueen films.



“The First Cut Is The Deepest”

To celebrate the release of her 2003 compilation The Very Best of Sheryl Crow, the singer recorded the Cat Stevens song “The First Cut Is The Deepest.” It would become one of her biggest hits since “All I Wanna Do.” The video—directed once again by Wayne Isham—boasts a western aesthetic, with Crow playing her guitar and riding horses amidst the backdrop of the canyon lands of Utah. The country western vibe of the song and video also earned Crow a Top 40 Country hit, her first.