40. Stephen Malkmus, “Jenny and the Ess-Dog” (2001)
After the 1999 breakup of alt-rock critical darlings Pavement, Malkmus continued to pursue his ever-peculiar muse with songs that often boasted his cryptic sense of humor yet sometimes added an unexpected depth and poignancy. That was never truer than on this song, about a May-December romance between a slumming hipster rich girl and a “man in a ’60s cover band.” Alas, the romance doesn’t last and the story ends with him busing tables and Jenny starting pre-law. Always a master of little details, Malkmus signifies Jenny’s final rejection of her less conservative ways with the decision to remove her “awful toe rings.”
39. Courtney Love, “Mono” (2004)
“Did you miss me?” asks Courtney Love not long into “Mono,” a should’ve-been-comeback single whose greatness no one could have predicted or expected. After all, it had been 10 very messy years since Live Through This, and for her to pull this out of the bag deserves a Rudy-like slow clap—even if that’s all wrong for the song’s blistering tempo. Bizarrely, she’d revert to using the Hole moniker (despite not including any other members) for 2010’s swiftly forgotten Nobody’s Daughter.
38. Robert Plant, “Big Log” (1983)
It takes a strong man to resist the constant demands for a Led Zeppelin reunion as steadfastly as Robert Plant has. Instead, Plant’s career has been amazingly varied, ranging from the sock-hop schmaltz of The Honeydrippers and a Grammy-winning collaboration with bluegrass star Alison Krauss to the mix of rock, folk, and Middle Eastern music on albums like this year’s Carry Fire. But with its Zep-like grandeur, this evocative hit from his second solo album has an obvious appeal for any boomer who longed to replicate Plant’s godlike locks.
37. Diana Ross, “Upside Down” (1980)
Motown boss Berry Gordy made no bones about who he thought was the true star of The Supremes, even if Ross wasn’t the strongest vocalist. Nor did she disagree. Later fictionalized in the musical Dreamgirls, Ross’ ambitions were first signaled when her group became Diana Ross & The Supremes before she became a full-fledged solo diva by the mid-’70s. And while the advent of disco could have rendered her obsolete, it became another chance for her to show her tenacity, collaborating with Chic’s Nile Rodgers and Bernard Edwards on one of several impeccable demonstrations of her new dancefloor dominance.
36. Dennis Wilson, “River Song” (1977)
With disco at its commercial zenith and punk galvanizing the underground, the music world of 1977 had zero interest in a sumptuously produced and orchestrated solo album by the drummer of The Beach Boys. Indeed, it took a few decades, and Dennis’ death, for Pacific Ocean Blue to get its due. That includes its opening track and lead single, a deeply melancholy slice of SoCal decadence.
35. Ice Cube, “It Was a Good Day” (1992)
Ice Cube was at the peak of his powers in the years that spanned his 1989 departure from N.W.A. and his first Friday movie in 1994, the stoner flick being the first sign of the non-threatening Cube who’d suit Hollywood family comedies just fine. The single that helped make The Predator his biggest seller was a nostalgic, Isley Brothers-flavored tribute to all the things that made a day great, from breakfast with his mom, to basketball with his homies, to a few long-sought-after hookups, to the fact that “nobody I know got killed in South Central L.A.” Only a few months after the Rodney King riots, the significance of that last line was impossible to miss.
34. Syd Barrett, “Terrapin” (1970)
Pink Floyd’s co-founder was arguably the most significant architect of British psychedelia until the abundance of LSD trips took their toll on his fragile psyche. Begun after his forced departure from the band, much of Syd Barrett’s first solo album, The Madcap Laughs, brandished the same cracked-up-nursery-rhyme appeal of early Floyd singles like “See Emily Play.” But the oddly chilling likes of “Terrapin” suggested that something had broken deep inside.
33. Q-Tip, “Vivrant Thing” (1999)
Sly, sexy, and funky as hell, “Vivrant Thing” is a precisely calibrated club banger unlike anything in A Tribe Called Quest’s back catalog—but irresistible all the same. Mostly produced by Q-Tip and Jay Dee, his solo debut, Amplified, had a few tracks that were nearly as hot. Yet Q-Tip would make only two more solo albums—plus the reunited Tribe’s 2016 masterpiece We Got It from Here… Thank You 4 Your Service—in the two decades since, eschewing the fur-coat-wearing, block-rocking playa image he flirted with here.
32. Richard Ashcroft, “A Song for the Lovers” (2000)
With “Bittersweet Symphony” and “Lucky Man,” The Verve became one of Britpop’s international breakout acts. Yet the band’s constant turmoil prevented them from following through. No wonder frontman Richard Ashcroft took so many big swings on 2000’s Alone With Everybody, launched with a single that boasted all of the sweep and scope of The Verve’s most epic efforts.
31. Big Boi, “Shutterbugg” (2010)
While it’s been hard to subsist on nothing but occasional guest spots by Andre 3000 in the 11 years since OutKast’s original split, it’s not been so painful for fans who knew which man really brought his A game to Speakerboxxx/The Love Below. With his first legit solo smash, Big Boi didn’t see any reason to start skimping on the bounce or the swagger.