In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
Writing about his late friend David Berman in Rolling Stone a few weeks ago, Rob Sheffield mentioned that Berman had a great line about Paul Simon’s “50 Ways To Leave Your Lover.” Paul Simon, Berman wrote, was wrong. There are only two ways to leave your lover: “You can up and leave, Steve. Or you can go to your grave, Dave.” Great lines tend to inspire great lines. And “50 Ways To Leave Your Lover” has a whole lot of great lines.
Up until their 1970 breakup, Simon & Garfunkel were an absolutely dominant commercial force — something they achieved, at least in part, by convincing everyone that they were more studiously self-serious than all their peers. Simon & Garfunkel were more playful than they get credit for being, but for a lot of self-impressed ’60s kids — kids like my parents — they were poets, and that was a big part of the appeal. When people like Bob Dylan were transforming into elusive rapscallions, Simon & Garfunkel were still singing expansive profundities in choirboy harmony. Simon & Garfunkel hit #1 three times — all with songs that must’ve been quoted on countless yearbook pages. So maybe it’s cosmically appropriate that the one time Paul Simon hit #1 on his own, he did it with what might be the single silliest divorce song ever put on record.
After Paul Simon split with Art Garfunkel, he went off on one hell of an artistic journey. Simon had already started to play around with different global sounds toward the end of Simon & Garfunkel, but when he started putting out solo records, Simon pretty much became a kid in a candy store. He tinkered with reggae, with gospel, with Peruvian folk music. He set these bold, vivid, joyous sounds to breezy, nostaliga-drenched lyrics, clearly taking nothing too seriously. And those songs landed.
Through the early ’70s, Paul Simon remained a pop-chart staple. 1972’s cheery death-meditation reggae experiment “Mother And Child Reunion” peaked at #4. (It’s a 9.) 1972’s “Kodachrome,” a bouncy Muscle Shoals-recorded dismissal of all the crap that Simon learned in high school, made it up to #2. (It’s an 8.) Later that same year, Simon again made it up to #2 with the giddy, gospel-infused “Loves Me Like A Rock.” (It’s another 8.) In Simon & Garfunkel, the knock on Simon was that he wasn’t as good-looking or as charismatic as Art Garfunkel. But when set free to do whatever the hell he wanted, Simon was a star.
So Simon was all puffed up with massive and well-earned confidence when he recorded his late-1975 album Still Crazy After All These Years. It’s a great piece of work, full of little jazz and R&B flourishes that never overwhelm Simon’s melodies. At the time, the big news about Still Crazy was probably the one-off Simon & Garfunkel reunion on the wanderlust-driven lead single “My Little Town,” which peaked at #9. (It’s a 7.) But the album’s greatest legacy would turn out to be its silliest song.
Simon started to write “50 Ways To Leave Your Lover” as a sort of kids’ game. Earlier in 1975, the 33-year-old Simon and his first wife Peggy Harper had split up after six years of marriage. One day, Simon had their three-year-old son Harper at his apartment, and he was trying to teach Harper how to rhyme. That’s how he came up with the chorus, with all its rattled-off names: “You just slip out the back, Jack / Make a new plan, Stan.” (Harper is now doing just fine for himself as a singer-songwriter, so the lesson must’ve worked.) In a 1975 interview, Simon admitted that “50 Ways” is “basically a nonsense song.”
He’s wrong, of course. “50 Ways” is actually a dazzling little piece of storytelling. A man is having an affair, but he’s dithering about ending his main relationship. He wants out, but he doesn’t know how to go through with it. The other woman wants him to hurry up and get the fuck out, and she tells him that he needs to do it. But she never comes out and says that. Instead, she frames it as helpful advice: “She said, ‘It grieves me so, to see you in such pain / I wish there was something I could do to make you smile again.'” And then she tells him to just do it — to act, to be decisive, to do any of the 50 things you can do to become single again.
Simon presents the whole thing as a dialog, almost a scene from a movie. He never offers any details on his own narrator or on the woman who’s helping him in his struggle to be free. Simon doesn’t even say if he’s cheating with this other woman; it’s just heavily implied. In that simple stretch of dialogue, we can infer the entire situation that this man has made for himself. And we can see the light slowly dawning on him. He can do it. He can leave. It’ll be fine. Simon said that he didn’t write “50 Ways To Leave Your Lover” about his ex-wife. But when you come out with a song like that a few months after your first divorce, you’re telling us something.
In any case, “50 Ways To Leave Your Lover” remains one of the few divorce songs that isn’t mired in reflection or self-pity. Instead, it’s a sly exultation, a wink at the whole idea that there can be freedom after marriage. The divorce rate was skyrocketing by the mid-’70s, so maybe that had something to do with the song’s popularity. A whole lot of the baby boomers who’d gotten married straight out of college — as well as those who, like Simon, were slightly older than the boomers — were starting to figure out that they didn’t have to stay with the same person for their entire lives. Heard from a certain perspective, “50 Ways To Leave Your Lover” works as a celebration of that ability to get yourself free, and of the loss of stigma around it. (All those boomer divorces, it’s probably worth noting, did a real number on my generation of kids. But my parents are still together, and it’s not like I’m any less fucked up than my peers, so maybe all that freedom was ultimately a good thing.)
Simon wrote “50 Ways To Leave Your Lover” to the beat of a drum machine. (I’ve now learned that a lot of ’70s songwriters did this, and I find that delightful.) When Simon recorded the song, the great studio drummer Steve Gadd came up with an intricate marching patter-riff. Simon, wanting to keep the song simple, arranged the entire track around those drums, which was a smart thing to do. “50 Ways To Leave Your Lover” is a casually funky track, one that keeps bubbling throughout. The chorus doesn’t explode; it effortlessly slides right in. And when the chorus subsides, everything comes back to that drum riff again. That beat is the reason that “50 Ways” has been sampled dozens of times. (See below.) It’s also probably what keeps “50 Ways” from ever sounding vicious or callous, even though it’s really both.
Incidentally, all three of the backup singers on “50 Ways To Leave Your Lover” — Valerie Simpson, Patti Austin, and Phoebe Snow — were prominent musicians in their own right. Valerie Simpson was the Simpson of Ashford & Simpson, who had already written “Ain’t No Mountain High Enough” and produced the 1970 Diana Ross version, which had been Ross’ first solo #1 hit. Simpson had also released a couple of solo albums on Motown; later on, Ashford & Simpson, as artists, would peak at #12 with 1984’s “Solid.” The singer-songwriter Phoebe Snow, who’d been touring with Simon all year, had already peaked at #5 with 1975’s “Poetry Man.” (It’s a 6.) And Patti Austin will eventually show up in this column, Simpson, Snow, and Austin don’t really get a whole lot of opportunity to show off on “50 Ways,” but that’s still a whole lot of talent in one room.
Simon never got to #1 again after “50 Ways To Leave Your Lover,” but he did just fine for himself anyway. The night that “50 Ways” was knocked out of the #1 spot, Simon’s Still Crazy After All These Years won the Grammy for Album Of The Year. Stevie Wonder had won the two previous Album Of The Year awards back-to-back, and in his acceptance speech, Simon thanked Wonder for not releasing an album that year. (Wonder would win again the following year.)
Simon got married twice more — first to Carrie Fisher, then to Edie Brickell. (Brickell’s highest-charting sing, 1988’s “What I Am,” peaked at #7. It’s an 8.) Simon also kept making hits, and he started acting; his first part was a pretty prominent role in 1977’s Annie Hall, the Woody Allen movie that would win Best Picture the following year. In 1980, Simon made the classic pop-star imperial hubris movie: He wrote and starred in One-Trick Pony, a movie about a fading folk-rock star. Critically and commercially, One-Trick Pony was an absolute failure. But Simon also did the movie’s soundtrack, and one of its songs, “Late In The Evening,” would turn out to be Simon’s final top-10 hit. (It peaked at #6, and it’s a 9.)
Simon wasn’t a big presence on the singles charts in the ’80s, but he still sold absurd numbers of albums. Simon’s 1986 masterpiece Graceland, for instance, was Billboard‘s #2 album of 1987. That year, Graceland didn’t sell as many copies as Slippery When Wet, but it sold more than Licensed To Ill or Control or The Joshua Tree. So that’s still pretty good.
GRADE: 9/10
BONUS BEATS: Eminem’s Slim Shady EP, from 1997, was an underground record that sold basically nothing, but it introduced the bloodthirsty character that would make Eminem so overwhelmingly famous. A lot of the tracks on The Slim Shady EP ended up on 1999’s huge Slim Shady LP. One of the EP tracks that didn’t appear on the album was “Murder, Murder,” on which Em rapped over a sample from “50 Ways To Leave Your Lover.” Here’s that:
(Eminem would use a “50 Ways To Leave Your Lover” sample again on the 2011 loosie “50 Ways.” Em will, of course, appear in this column many times. The list of other rappers who have used “50 Ways To Leave Your Lover” samples includes Kool Moe Dee, Andre Nickatina, DJ Quik, Diamond D, Common, will.i.am, Logic, Ab-Soul, and a whole lot of others.
BONUS BONUS BEATS: Here’s the cover of “50 Ways To Leave Your Lover” that the electroclash producer Playgroup and the dancehall growler Shinehead released in 2001:
BONUS BONUS BONUS BEATS: On his 2008 mixtape A Kid Named Cudi, Kid Cudi tweaked “50 Ways To Leave Your Lover,” transforming it into “50 Ways To Make A Record.” Here it is:
(Kid Cudi’s highest-charting single, 2008’s “Day ‘N’ Night,” peaked at #3. It’s a 10.)
BONUS BONUS BONUS BONUS BEATS: Here’s Julia Louis-Dreyfus singing a “50 Ways To Leave Your Lover” parody that will get her into some political trouble on a 2013 episode of Veep:
BONUS BONUS BONUS BONUS BONUS BEATS: Here’s Neneh Cherry’s 2018 track “Faster Than Truth,” which producer Four Tet built from a sample of the “50 Ways To Leave Your Lover” drums:
(Neneh Cherry’s highest-charting single, 1988’s “Buffalo Stance,” peaked at #3. It’s a 10.)
THE NUMBER TWOS: Donna Summer’s endless psychedelic fuck-disco odyssey “Love To Love You Baby” peaked at #2 behind “50 Ways To Leave Your Lover.” I love to love it, and it’s a 10.
