The Very Best of Sheryl Crow: Celebrating a Rock & Roll Icon
Last Friday, 9-time Grammy winning rock-and-roll icon Sheryl Crow released her 10th and reportedly final album, Threads. The long in-the-works collection features collaborations with a remarkable array of music legends across a number of genres, including (but not limited to) Johnny Cash, Keith Richards, Willie Nelson, Sting, Eric Clapton, Mavis Staples, Joe Walsh, Kris Kristofferson, Emmylou Harris, James Taylor, Bonnie Raitt, Vince Gill, Neil Young, and Brandi Carlisle. The album serves as a reminder not just of Crow’s skills as a songwriter, vocalist, and guitarist but also of the profound respect she has commanded in the music industry since the release of her debut album Tuesday Night Music Club just over 26 years ago.
Over the past quarter century, Crow has released a handful of iconic pop hits and had high profile romantic relationships with famous men like Eric Clapton, Lance Armstrong, and Owen Wilson. Unfortunately, that’s all that most casual music fans know about her. What many do not realize is that she has unquestionably established herself as a remarkably skilled and prolific songwriter, a tireless and committed live performer, a superb guitarist, and a champion of feminist and progressive causes. She has collaborated with some of the most well-respected musicians of the 20th century (including getting her start as a backup singer for Michael Jackson) and expertly switches between genres as diverse as pop, rock, alternative, country, blues, folk, soul, and funk.
I have been an admirer of Crow’s since I bought Tuesday Night Music Club on cassette tape when I was 9 and danced to “All I Wanna Do” in our basement. The monumental release of Threads inspired me to go back and revisit her catalogue as a whole and chronicle my picks for her greatest songs. I was originally going to just do 26, reflecting the number of years since her debut, but it turns out Sheryl Crow’s greatness couldn’t be contained to a list any smaller than 50.
Without further ado, here are my picks for the very best songs by Sheryl Crow.
50.) “Drunk With the Thought of You” (Detours, 2008) Perhaps the most restrained and romantic song Crow ever crafted, it unabashedly captures the throes of true love in two and a half sweet minutes.
49.) “Lonely Alone” (Threads, 2019) Crow has long been a friend and collaborator of iconic country-folk singer Willie Nelson (now 86 years old), so it’s surprising that their first recorded duet of an original song came so late in their respective careers. But it was worth the wait. Their voices harmonize superbly, the melody is delightful, and the lyrics about two down-on-their-luck bar patrons contemplating a tryst are nuanced.
48.) “Roses and Moonlight” (100 Miles from Memphis, 2010) This moody, sensuous closeout to her 7th album (which was dedicated to Memphis soul) is hypnotic and hook-driven for the first 3 minutes before a radical changeup in tempo and arrangement turn the song on its head.
47.) “Love is Free” (Detours, 2006) This funky, folksy track was sonically and lyrically inspired by the people of New Orleans — particularly, their resilience in the aftermath of Hurricane Katrina. But it is anything but solemn. In fact, it is a joyous and playful anthem.
46.) “Tomorrow Never Dies” (Tomorrow Never Dies Soundtrack, 1997) The winner among 12 songs submitted for consideration for the 18th James Bond film, the song was negatively reviewed upon release despite subsequent Golden Globe and Grammy nominations. I find that time has been kind to the song. Although it doesn’t pack the same emotional punch as some other Bond anthems, I think that is mainly due to the fact that it simply isn’t trying to. Like the film(s), the song is all well-calibrated attitude and glitz. And it works.
45.) “Killer Life” (Tuesday Night Music Club Deluxe Edition, 2009) This previously unreleased track from the Tuesday Night Music Club sessions was included on the 2009 deluxe edition and it’s confounding why it didn’t make the cut of the album — its spoken word verses are lyrically provocative and its hook is hypnotic.
44.) “Be Myself” (Be Myself, 2017) “Saw my shrink today, he said, ‘Girl I can’t help you/ I’ve been seeing you so long, but nothing has changed/ You tried Adderall and alcohol, sadly the fact remains/ You’re terminally normal, I’m sorry to say.’” The opening lines of the title track from her 9th album find Crow entering her “I-have-zero-f***s-left-to-give-when-it-comes-to-impressing-people” phase and the result is a catchy and cathartic anthem (and album).
43.) “Try Not to Remember” (Home of the Brave Soundtrack, 2006) The military transition drama that it served as the theme for may have been a major critical and commercial failure, but the soulful Golden Globe-nominated song about the wounds of war soars.
42.) “Picture” (Kid Rock’s Cocky, 2002) Even with the increasingly repugnant politics and repulsive persona of Kid Rock in mind, this folksy duet chronicling a pair of lovers ineffective and self-destructive attempts to move on after their breakup still packs a punch.
41.) “Diamond Ring” (Detours, 2008) Crow’s very public breakup with (since disgraced) cycling legend Lance Armstrong inspired this gut-wrenching confessional that features a vocal performance so raw that it’s hard to believe it was recorded in a studio and not on her bathroom floor at 3am after a couple of bottles of wine.
40.) “Summer Day” (100 Miles from Memphis, 2010) This soulful, nostalgia-fueled track (which served as the first single for her 7th album) captures the mood of a summer reverie like few others.
39.) “Weather Channel” (C’mon C’mon, 2002) It seems somehow fitting that Crow’s most pop-oriented album to date closed with one of the least pop songs she’s ever recorded — a minimalist firsthand account of clinical depression that features harmonies from country legend Emmylou Harris. I can’t recall a song that lyrically or sonically captured depression so astutely or hauntingly (Sample lyric: “I got lab coats/ Who will bring me a panacea/ While I’m watching the Weather Channel/ Waiting for the storm.”)
38.) “Sweet Rosalyn” (Sheryl Crow, 1996) This funky track off of Crow’s second album exquisitely incorporates Los Lobos saxophonist Steve Berlin and tells the intriguing story of a hard-living woman running away from love. It also features one of my favorite lyrics she’s ever written: “She got a number off the bathroom wall/ She was looking for a good time so she made the call/ Got a strangely calm voice on the other line/ Sneaky little priest tryin’ to reach out to the swine/ He said, ‘Hello my name is Father Tim/ Seems to me your zeal for this life has been wearing a little thin.’”
37.) “Run Baby Run” (Tuesday Night Music Club, 1993) The first single and opening track from her first album, this song tells the story of an emotionally wrecked woman from her tumultuous childhood to her adult life of one night stands and does so with a terrific hook and commanding vocals. It was a bold start to her legendary career.
36.) “It’s Only Love” (C’mon C’mon, 2002) This atmospheric song about the complexity and futility of love starts quietly and builds to an emotional climax over 5 glorious minutes. (Fun fact: That’s Oscar-winning actress and GOOP founder Gwyneth Paltrow on backup vocals.)
35.) “The First Cut is the Deepest” (The Very Best of Sheryl Crow, 2003) Crow’s last major hit came 10 years after her debut with this cover of the timeless Cat Stevens’ heartbreak ballad. Its naked desire to appeal to the adult contemporary and pop-country crowd is slightly off-putting but it nevertheless is a very solid record that packs an emotional punch.
34.) “Diamond Road” (C’mon C’mon, 2002) This uncharacteristically heartwarming track features timeless lyrics, nuanced orchestration, and harmonies from the one and only Stevie Nicks.
33.) “Our Love is Fading” (100 Miles from Memphis, 2010) With few exceptions, Crow is terrific at selecting the perfect mood-setting opening song for her albums. This is especially true here, with the frenetic, funky, heavily orchestrated, and sprawling 6-and-a-half minute track that finds Crow warning a tentative paramour that she won’t wait around forever.
32.) “Detours” (Detours, 2008) The title track of Crow’s sixth album is this bouncy, guitar driven song that is positioned on the album as the bridge between the blistering sociopolitical commentary that marks the first half and the bold self-exploration that marks the second half. The lovely melody belies the plaintive lyrics, in which a woman so beaten down by past loves turns to her mother for advice on how to keep looking for someone worthy of her.
31.) “The Story of Everything” (Threads, 2019) I can imagine that some may have found this track from her latest album to be bombastic and even cringe-inducing at times. But after repeated lessons, I find it to be quite masterful. It is epic in scope and complexly arranged, with the incorporation of Crow’s lyrics about the racial divides in modern day America with a rap by Chuck D, stirring guitar work by Gary Clark Jr., and the impeccable vocals of Andra Day.
30.) “Mississippi” (The Globe Sessions, 1998) Sheryl Crow has recorded numerous covers throughout her career, but it is exceedingly rare that she recorded an original song offered to her by another songwriter. But I suppose exceptions to the rule are to be expected when the song comes from Nobel Prize winner Bob Dylan. Crow cleverly rearranged the song to fit the musical style of The Globe Sessions and expertly delivers the complex lyrics.
29.) “Can’t Cry Anymore” (Tuesday Night Music Club, 1993) This track off of her debut album emphasizes the need to keep fighting despite a multitude of setbacks (e.g., breakups, poverty, drug addiction). The message is deepened by a gritty, hard-edged vocal performance that encourages a cathartic scream-along.
28.) “Soak Up the Sun” (C’mon C’mon, 2002) The lead single off of Crow’s fourth album was a huge hit for her on the pop and adult contemporary charts. And it’s not hard to see why: it finds Crow in the fun, frothy, easygoing pop mode for arguably the first time since “All I Wanna Do.” Compared to the rest of the album — and the rest of her hits — it feels a bit slight, but it goes down like a glass of cold lemonade on a hot summer day.
27.) “Prove You Wrong” (Threads, 2019) This high energy country-pop ditty is a straightforward delight that makes excellent use of three superb musicians — Crow, Stevie Nicks, and Maren Morris. It would have been right at home on Fleetwood Mac’s “Say You Will” and, given my admiration for that underrated album, that is high praise indeed.
26.) “Rest of Me” (Be Myself, 2017) Subtly confounding lyrics about jaded adults’ approach to love and a terrific hook fuel this uptempo track, which is a pure pleasure from start to finish.
25.) “Out of Our Heads” (Detours, 2008) Crow’s desperate plea for world peace amidst genocide, terrorism, and other manifestations of hate, this song perfectly captures the spirit and intentions of her most ambitious album. Fittingly, it also is heavily influenced by global musical styles and features a commanding, emotional vocal performance.
24.) “Anything But Down” (The Globe Sessions, 1998) A woman’s realization that she is futilely devoted to a man who doesn’t bring her anything but down fuels a near-perfect pop/rock song.
23.) “Steve McQueen” (C’mon C’mon, 2002) Crow won a well-deserved Grammy for her vocal performance on this hard-edged, high-energy gem about her intense desire to hightail it out of the increasing disillusionment of the modern world.
22.) “Give It To Me” (Feels Like Home, 2013) In my opinion, Crow’s 2013 album Feels Like Home — which found her fully embracing country music — is one of her finest and most underappreciated works. This track is one of the finest on that collection. The lyrics, vocals, and arrangement work together beautifully to capture the intense longing of a woman in love with a hesitant man (a favorite theme of hers).
21.) “Members Only” (The Globe Sessions, 1998) With its unique blend of electric guitar, percussion, and synthesizers, this is one of the most aggressive and angriest songs in her catalogue (and, to be clear, that is very much a compliment).
20.) “Live Wire” (Threads, 2019) The best song on Crow’s ambitious 10th and final album is arguably her most blues-inspired song ever and to commemorate the occasion she brought on board two of the living legends of the genre — Mavis Staples and Bonnie Raitt. Everything about this timeless song works.
19.) “I Shall Believe” (Tuesday Night Music Club, 1993) The final track off of her debut album is often used as the encore to Crow’s concerts despite the fact that it was never released as a single. It’s easy to see why she chose it — it is haunting and mournful as it builds up to its emotional climax.
18.) “Waterproof Mascara” (Feels Like Home, 2013) Some may understandably take issue with the traditional gender norms espoused by the song, but nevertheless it is an unabashed heartstring-puller about the pain of watching a child grow up without a father. It is beautifully performed, covers unique thematic territory, and is very cleverly written (e.g., “And so I wear waterproof mascara/ There’s things you shouldn’t see when you’re a kid/ Thank God they make waterproof mascara/ ’Cause it won’t run like his daddy did.”)
17.) “Heartbeat Away” (Be Myself, 2017) Growling vocals and an aggressive hard rock arrangement perfectly accompany Crow’s incisive and blistering story of the morally bankrupt men whose greed and arrogance are rapidly leading our world toward doomsday.
16.) “It’s So Easy” (C’mon C’mon, 2002) Crow has partnered with a number of music legends for memorable duets, but no collaboration worked better than this one with Eagles frontman Don Henley. In just under 3 and a half minutes, they lay bare the beauty and pain of a couple’s illicit affair.
15.) “Calling Me When I’m Lonely” (Feels Like Home, 2013) The highlight of her massively underrated foray into country, this immensely relatable song about a man who knows the exact right ways to exploit a woman’s loneliness is pure pop-country perfection and should have been a massive hit.
14.) “The Difficult Kind” (The Globe Sessions, 1998) Coming in at over six minutes, this guitar-fueled, regretful lament about her role in a disintegrating romance is one of the most epic songs Crow ever recorded. It also features some of her most aching lyrics (e.g., “Oh, ball-breaking moon and ridiculing stars/ Oh, the older I get, the closer you are/ Don’t you got somewhere, that you need to be/ Instead of hanging here making a fool of me?”).
13.) “Everyday is a Winding Road” (Sheryl Crow, 1996) One of Crow’s most popular and iconic songs, this uptempo pop-rock ditty begs for a sing-along and shows off her penchant for writing a hook better than just about any song she ever composed. (Fun fact: The late legend Prince loved the song so much he performed it with her live and then subsequently released a cover.)
12.) “All I Wanna Do” (Tuesday Night Music Club, 1993) The song that launched Sheryl Crow into the stratosphere — and won her two of her nine Grammys — is one of the finest pop songs of the 1990s and an earworm for the ages. Although the lyrics heavily incorporate an obscure poem (“Fun” by Wyn Cooper) it nevertheless is a wholly original musical creation.
11.) “If It Makes You Happy” (Sheryl Crow, 1996) This punk-tinged rock anthem may have exceedingly nonsensical lyrics, but its Grammy-winning vocal performance and terrific production make it a highlight in her catalogue.
10.) “Gasoline” (Detours, 2008) This remarkably ambitious, explosively angry, and wickedly clever protest song finds Crow predicting a not-too-distant future when the devastating environmental, economic, and sociopolitical effects of governments’ greedy reliance on unsustainable fossil fuels reach the breaking point.
9.) “Always On Your Side” (Wildflower, 2005) Crow’s fifth album is my least favorite (note that this is the only song from the album that made the list), but its entire existence is justified by the presence of this song. The original version featuring just Crow’s vocals is far and away the highlight of the album and the re-recording that repurposed the song as a duet with Sting sends the song soaring into the stratosphere. It’s one of the most poignant songs she has ever written.
8.) “A Change Would Do You Good” (Sheryl Crow, 1996) Similar to “If It Makes You Happy,” this song features opaque lyrics comprised of seeming non-sequiturs delivered over a distinctive and memorable musical arrangement. In contrast to “If It Makes You Happy,” it is higher energy, more soulful, and features a killer bridge (“I’ve been thinking ‘bout catching a train/ Leave my phone machine by the radar range/ ‘Hello it’s me, I’m not at home/ If you’d like to reach me, leave me alone’”).
7.) “Leaving Las Vegas” (Tuesday Night Music Club, 1993) Although it remains unclear to what degree this song (the first single of Crow’s to chart on the Billboard Hot 100 ) is autobiographical or based on the book of the same name by the late John O’Brien (who died by suicide the year the song was released), the brilliant lyrics, plaintive delivery, and bold arrangement feel quintessentially Crow.
6.) “There Goes the Neighborhood” (The Globe Sessions, 1998) This infectious, horn-fueled rocker includes references to the Unabomber, dropping acid, Fiona Apple’s music video for “Criminal,” and the vapidity of the film industry, while incorporating Sir Peter Ustinov into the refrain. It is ambitious and wholly successful.
5.) “Redemption Day” (Sheryl Crow, 1996) Sheryl Crow has recorded dozens of powerful songs that could be considered political protests, but none are more exquisite than this absolutely wrenching indictment of the U.S.’s failure to intervene during the Bosnian War. Its brilliant and incisive lyrics, mournful arrangement, and appropriately restrained vocal performance make this one of the most underrated songs of the past quarter century. (Well, if you can consider a song that Johnny Cash loved enough to record on his final album to still be underrated.)
4.) “C’mon C’mon” (C’mon C’mon, 2002) This pop-rock slow burn finds Crow begging a wayward lover to come back and break her heart one more time because even though she knows better she just can’t help herself. The combination of her aching vocal performance (backed by the one and only Stevie Nicks), the eminently relatable lyrics, the indelible hook, and the cathartic bridge (“You took the best of me/ And threw it away/ Too bad the rest of me/ Still wants you to stay”) are pure perfection.
3.) “Home” (Sheryl Crow, 1996) “I woke up this morning/ And now I understand/ What it means to give your life to just one man/ Afraid of feeling nothing/ No bees or butterflies/ My head is full of voices/ And my house is full of lies.” It is hard to name a song with more poignant opening lines and yet the song somehow increases in dramatic power from there, all the way through the extended vocal-free outro.
2.) “Strong Enough” (Tuesday Night Music Club, 1993) The raw vocals, minimal acoustic arrangement, and short run time of this song made it an outlier on her debut, but it is nevertheless the best song featured on it. The lyrics take the form of a monologue delivered by an emotionally overwhelmed woman all too aware of her flaws to a man who wants to get close but she fears may not know what he’s getting into. It remains one of Crow’s very finest hours vocally and lyrically and the fact that legendary artists as diverse as Stevie Nicks, the Dixie Chicks, and Beyonce have subsequently performed it only underscore its universality.
1.) “My Favorite Mistake” (The Globe Sessions, 1998) Precious few songs are truly perfect, but “My Favorite Mistake” is undoubtedly a member of that very small group. The lead single from her third album, it captures the ambivalence and heartbreak of a woman in love who knows that her lover is unfaithful. The lyrics are exceedingly clever and the vocal performance is flawless. This is Sheryl’s finest hour in a career filled with many highs.
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