‘60 Songs That Explain the ’90s’: ‘If It Makes You Happy,’ Sheryl Crow

Grunge. Wu-Tang Clan. Radiohead. “Wonderwall.” The music of the ’90s was as exciting as it was diverse. But what does it say about the era—and why does it still matter? 60 Songs That Explain the ’90s is back for 30 final episodes (and a brand-new book!) to try to answer those questions. Join Ringer music writer and ’90s survivor Rob Harvilla as he treks through the soundtrack of his youth, one song (and embarrassing anecdote) at a time. Follow and listen for free on Spotify. In Episode 94 of 60 Songs That Explain the ’90s—yep, you read that right—we’re covering Sheryl Crow and “If It Makes You Happy.” Below is an excerpt of this episode’s transcript.

Sheryl Crow was born in February 1962, the day jazz saxophonist Leo Parker died. That’s all I got. She was born in Kennett, Missouri, in the southeastern corner, in the bootheel of Missouri, near other modest towns and small communities with names like Frisbee, Cooter, Braggadocio, Bragg City, Holland, Europa, Austin, and Hollywood. This is a part of Missouri often at great pains to trick you into believing you’re not actually in Missouri.

She had a reasonably idyllic childhood, Sheryl, as rock stars go. Supportive and super-musical parents. (Her parents were in a swing band together.) In high school she was a cheerleader and a baton twirler. (Sheryl demonstrated the baton twirling on the Today show once, very charming.) She graduated from the University of Missouri in 1984 with a degree in music education. (Mizzou named a choral hall after her in 2022.) She taught fourth grade and sang in various bar bands and got engaged to a born-again-Christian singer dude who told her, quote, “If you’re not singing for the Lord, we can’t be together,” end quote. (They ain’t together.) She decides to go for it. She moves out to Los Angeles, the one in California. She makes $42,000 singing a McDonald’s jingle. She hawks a demo tape around town to no particular avail. Then she bluffs her way into a gig singing backing vocals for Michael Jackson, and voila, Sheryl Crow the former fourth-grade teacher from Kennett, Missouri, is onstage at Wembley Stadium (the one in London) in a giant wig singing “I Just Can’t Stop Loving You” with the King of Pop. God bless.

This is one of those deals where if you have even a casual interest in Sheryl Crow you’re likely aware that she got her big break singing backup vocals for Michael Jackson, but even when you’re on YouTube or whatever and you’re looking right at her, and looking right at him, and looking right at him touching her flirtatiously to the rapturous cheers of the crowd at Wembley Stadium as they sing the quite famous Michael Jackson song that you can clearly hear them singing together—even then, some small stubborn compartment of your brain refuses to fully process this information. Or maybe that’s just me. My buddy Mike was complaining to me once about people who misuse the surreal, people who abuse the word surreal and overuse it to mean anything that’s, like, slightly weird. And Mike’s like, You can’t just—surreal has to be something that’s technically possible but is never gonna actually happen, like, I wanna go swimming, so I go to the pool, and there’s a horse in the swimming pool. What’s a horse doing in the swimming pool? That is surreal. Sheryl Crow singing a duet with Michael Jackson is the horse in the swimming pool.

It’s her. No one is saying it’s not her. Her wig is voluminous and like super-’80s but it’s not necessarily necessary, given what will soon be the quite famous voluminousness of Sheryl Crow’s real hair. It trips me out, man. Sheryl got a lot of unwanted tabloid attention, of the Michael Jackson’s Secret Lover variety, and that tripped her out. After that she sang backup for Don Henley—see, that’s not surreal at all. That makes all kinds of sense. According to MTV, in 1999 “Boys of Summer” by Don Henley was the 67th best music video made at that point, and the 66th best music video was “(You Gotta) Fight for Your Right (To Party)” by the Beastie Boys. That’s funny. Don’t look back. You can never look back. Time for a solo career. Sheryl connects with a big-shot producer named Hugh Padgham—who’s worked with Phil Collins, Paul McCartney, the Police, solo Sting, bluh bluh bluh—and in the early ’90s Hugh and Sheryl cut an entire Sheryl Crow solo album that never comes out. The label scraps it. Too glossy, too produced, too ’80s, too, uh, Sting. Too much “It Must’ve Been Love” and not enough “Black Velvet,” y’know? That whole record’s on YouTube as well, but it’s more like a Baby Ruth in the swimming pool if you’ll forgive the expression.

By now Sheryl is dating a gentleman named Kevin Gilbert, and she’s playing keyboards in an L.A. rock band Kevin’s got going called Toy Matinee, and Kevin also introduces her to the Tuesday Night Music Club, a hard-drinking, acid-dropping, shit-talking, occasional songwriting, actual-Tuesday-night-meeting gang of multi-instrumentalist dudely bros—including David Baerwald, David Ricketts, Dan Schwartz, Brian MacLeod, and ringleader/producer Bill Bottrell—who’re all dude-broing the Tuesday night away in a local studio called Toad Hall. And these fellas welcome Sheryl into the fold on the third Tuesday, because, as Bill will later explain to Rolling Stone, given “the increasingly macho atmosphere that was developing in the room, it would be nice to have some female energy around that wasn’t so blockheaded.” Bill explains this in a 1996 Sheryl Crow Rolling Stone cover story where he says some much ruder things on account of the fact that by then this whole Tuesday Night situation has blown the fuck up. But yeah anyway Sheryl and the blockheads start writing some songs. Ooh, here’s one!

Another widely available but still hard-to-process Sheryl Crow fact is that the lyrics to “All I Wanna Do” are a poem she found, a poem called “Fun” written by a gentleman named Wyn Cooper, who was, as you can imagine, ultimately pretty psyched about this development. The lyrics to “All I Wanna Do” are the poem, like, near-verbatim. It’s remarkable. This is a more impressive feat than writing your own lyrics, if you ask me. It’s remarkable how few alterations Sheryl makes to the words, here, as she transforms a random guy’s poem into a Top 5 hit song. Even the part about it being Tuesday was already there.

See, now, this part is starting to trip me out, also. Even though there’s no way it happened this way, I’m still picturing unfamous Sheryl Crow in a bookstore reading this poem and then this super-famous Sheryl Crow song just appearing in a thought bubble over her head. It definitely didn’t happen that way because this song is not just her thought bubble, which is why the whole Tuesday Night situation is gonna blow the fuck up, but nonetheless.

This part’s verbatim, too. The only difference is these lines are not the last lines of the poem. What Sheryl Crow and her briefly merry band of blockheads realize—and this realization will help win “All I Wanna Do” the Grammy for Record of the Year—is that these should be the last lines of the song.

And then you just hammer at the chorus again. Perfect song. “All I Wanna Do” is the song that finally breaks Sheryl Crow. The song that makes her famous. It is not, however, the first single released off Tuesday Night Music Club. It is, in fact, the fourth single. And oooh, this is a fun game. I love this game. Let’s play the Botched Album Rollout game. The record label looked at Tuesday Night Music Club, and said, Which of these songs is gonna get 7 million people to buy this record, and their first guess, the first single, was “Run, Baby, Run.”

Great chorus, great song, great album opener, great opening line, not a great first radio single, relative, to, y’know, six other possible songs on this record. And the Botched Album Rollout is on. “Run, Baby, Run” doesn’t do so hot as a first single. So the label tries again. The label asks itself: What’s the second-best song on Tuesday Night Music Club? And here’s what they come up with.

The label goes with a slinky and confrontational tune called “What I Can Do for You,” which sounds like Maximum Don Henley to me, actually: the insinuatingly sleazy character study. And Sheryl Crow sings the hell out of it the way she sings the hell out of everything, and she is singing about sexual harassment, and predatory assholes in positions of power—predatory assholes in positions of power in the music industry, for example—and it is impressive how little ambiguity there is about what or really who Sheryl is singing about, and how sleazy this guy is who she’s portraying, but also how dopey this guy is, too, how inarticulate, how weak. Dig the line delivery here:

I love gosh that’s nice. Just the luminous trail of slime left behind by gosh that’s nice. It is a monumental achievement, how deliberately squirmy and unbearable “What I Can Do for You” is, and actually I’m getting into the monumental omnidirectional Fuck You of making this the second single. They shoulda given this song the Grammy for Fuck You of the Year.

When you put on Tuesday Night Music Club now, it’s divided almost exactly in half, between songs you’ve heard 10 billion times and songs you haven’t heard 10 billion times unless you’ve listened to this whole record 10 billion times. “I Shall Believe” is the last song, it’s not a huge hit song, but it’s a hit song to me, so it counts. And it’s a little funny to me that the first few attempted singles off this record do not come from the Super Famous and Ubiquitous half of this record, but the more important takeaway here is how hard, how lyrically hard the unfamous half of this record goes. You get to a song called “The Na-Na Song,” which is a full song but feels like a skit, like a goof, because it’s basically just Sheryl Crow rapping for three minutes. And maybe your tendency, listening to the whole album, is to view “The Na-Na Song” as a throwaway, as a breather, as a respite, as an odd and modest and merely functional bridge to the various super-famous songs that surround it, but then you focus on what Sheryl’s rapping and you suddenly realize that she’s rapping, “Eat sleep live die fucking record label” and then calling out three prominent men, all in like 10 seconds.

The three prominent men being G. Gordon Liddy, Clarence Thomas, and Frank DiLeo. Frank DiLeo’s dong, if I’m not mistaken. Frank DiLeo was Michael Jackson’s manager; Sheryl has spoken at length, and quite recently, about being sexually harassed by Frank DiLeo while she was on tour with Michael Jackson. She says Frank promised to make her a star. Maybe if I’d let him I’d have had a hit song. After this record came out Frank threatened to sue but did not. And what you really gotta worry about on Tuesday Night Music Club, if you’re a clueless predatory Gosh That’s Nice type, is what might happen if Sheryl Crow ever goes that hard on an actual hit song. Meanwhile, the record’s third single is “Leaving Las Vegas.” Here we go.

To hear the full episode, click here. Subscribe here and check back every Wednesday for new episodes. And to preorder Rob’s new book, Songs That Explain the ’90s, visit the Hachette Book Group website.