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Celebrating Prince: 15 Deep Cuts From the Purple One’s Vast Catalog

An almost incomprehensible loss hit the music world on April 21, 2016, when Prince died in his native Minnesota at the age of 57.

The incalculably talented and influential musical genius notched a massive run of hits on various Billboard charts during his nearly 40-year recording career, and he also left behind an imposing, rich catalog. His talent was so profound that he was often able to relegate flawless material to b-side status or leave it in his Vault entirely; a number of those previously shelved gems have seen public release in the years since his death.

From album deep cuts to b-sides to posthumous material from his Vault, here are 15 of our favorite less celebrated Prince songs.

“Gotta Stop (Messin’ About)” (1981)

A U.K. single that didn’t make much of an impact, “Gotta Stop (Messin’ About)” is nevertheless a must-hear slice of the Minneapolis sound. It’s funk meets synthpop meets New Wave with references to sex and masturbation aplenty. Prince stopped being outright filthy decades ago, but you’ll still need a shower after listening to this.

“Ronnie, Talk to Russia” (1981)

Just before deciding the nuclear holocaust was inevitable on 1999, Prince released the quickie political plea “Ronnie, Talk to Russia” on Controversy, urging Reagan to deescalate tensions with Soviet Russia. Delivered like a cutesy kids’ tune but sung with an underlying anxiety, Prince demonstrated that protest songs directed at presidents don’t have to be dull, sanctimonious affairs.

“Make-Up” (1982)

A deep cut from Vanity 6’s self-titled 1982 album, “Make-Up” was a a robo-sex kitten satire in their hands. But when the Prince Estate dug into his Vault for 2019’s Originals, which features his recordings of songs that eventually went to others (usually with his final say on production), this was one of the surprise highlights. With crisp hi-hats, a Kraftwerkian mechanical chill and a nervous synth line that would have felt right at home in Liquid Sky, “Make-Up” makes the case that Prince could have executed an entire album of ice-cold, drugged-out synth-pop had he been so inclined. For fans of “All the Critics Love U In New York.”

“Another Lonely Christmas” (1984)

Probably the saddest Christmas song ever, and definitely the most underrated Christmas song of all time. Prince reflects on sweet, erotic memories of a deceased lover, who died on Dec. 25, with his voice and piano growing increasingly despondent as the track works up to a heart-wrenching conclusion. At this point in his career, Prince was so good he could relegate classics like this to b-side status.

“Condition of the Heart” (1985)

While this isn’t one of the big hits from Around the World in a Day, it’s certainly one of that album’s best moments. Synths rarely sound spiritual in music (at least without sounding corny at the same time), but with Prince, all things are possible. His contemplative piano intro and space-y synths set the scene for one of the prettiest lovelorn songs in his catalog.

“Under the Cherry Moon” (1986)

While most people ignored Prince’s follow-up film to the wildly successful Purple Rain, that movie — Under the Cherry Moon — does boast a brilliant soundtrack in Parade. “Kiss” got most of the attention from that LP, but an equally durable song from Parade is the gorgeous, seductive ballad “Under the Cherry Moon.” With romantic ’40s vibes, this song demonstrates that Prince would have been an acclaimed songwriter had he been born in any decade.

“Bob George” (1987)

For reasons that may never be fully known, Prince recalled The Black Album just before its release in 1987. It would eventually see brief release in 1994 after years of bootlegging, which is as it should be. The admittedly bizarre but brilliant album features one particular highlight in “Bob George,” which finds Prince assuming the role of a violent misogynist while slamming Prince as “that skinny motherf–ker with the high voice.”

“Tick, Tick, Bang” (1990)

Graffiti Bridge is definitely one of Prince’s weaker albums, but anything Prince released still had touches of genius. One of the worthwhile tracks from this release is “Tick, Tick, Bang,” a leftover from Controversy sessions that includes a sample from Jimi Hendrix’s “Little Miss Lover.”

“It’s About That Walk” (1993)

While he mastered a variety of musical styles, Prince always sounded most relaxed when toying around with the old-school funk sounds that preceded his debut album by just a few years. This track, from the 1999 leftovers album The Vault: Old Friends 4 Sale, kicks off with sassy horns and a saucy lead vocal from Prince, who describes an “ass like a fine curved diamond” with so much attitude you can almost hear him winking through the speakers.

“Pheromone” (1994)

When Prince replaced the crisp drumming of his Revolution days with a more machine-like beat on some ’90s recordings, it didn’t always yield the best results. One exception is “Pheromone” from the 1994 album Come (yes, the album title means exactly what you think), which demonstrates that his funky, teasing falsetto can turn any song into a sweat-drenched sex romp.

“Billy Jack Bitch” (1995)

A sample of a man hysterically crying out “b-tch” (taken from a Fishbone song, no less) serves as the unlikely centerpiece for this sleazy funk jam from The Gold Experience. Rumors that this song was a takedown of a Minneapolis gossip columnist fueled interest back in ’95, but these days, “Billy Jack Bitch” is worth seeking out for the magnificent gospel-tinged organ solo, a squiggly fuzz-guitar riff and a punchy horn outro from the Hornheads (rechristened “Hornheadz” by Prince when they were in his presence).

“Dig U Better Dead” (1996)

Much like the overlong but nevertheless rewarding triple disc Emancipation album that also came out in 1996, Chaos and Disorder (released to fulfill contractual obligations with Warner Bros.) has its peaks and valleys. On one hand, there’s the unfortunately titled “I Rock, Therefore I Am”; “Dig U Better Dead,” however, is an underappreciated jam from his divisive mid-to-late ’90s run, a new jack swing throwdown with an irrepressible beat, some turntablist flair and that mix of thoughtfulness and sass that only Prince could pull off.

“Illusion, Coma, Pimp & Circumstance” (2004)

After a few years in the late ’90s where the musical genius seemed somewhat lost, the Purple One returned to the music that inspired him to start playing in the first place — hard-grooving party funk — on the 2004 album Musicology. “Illusion, Coma, Pimp & Circumstance,” a weird and witty tale of a sugar mama and her trophy boyfriend who “hips her to the funk in exchange for the finance,” is one of that LP’s standouts — and one of his late career highlights.

“Lolita” (2006)

As Prince moved from the secular to the spiritual later in life, he never quite left his profane urges entirely behind. One example is “Lolita” from 3121, a funky dancefloor throwback that found the Purple One considering cheating on his lady with a younger girl, but ultimately deciding against it with this cheeky little couplet: “Lolita, you’re sweeter / but you’ll never make a cheater out of me.”

“Lavaux” (2010)

For a scattershot LP like 2010’s 20Ten (which was distributed by U.K. print publications but never saw official U.S. release), it’s fitting that the best track is a three-minute tune inspired by a random lil wine region in Switzerland that tickled the Purple One’s fancy. With stakes this low, Prince was free to toss out one of the slinkiest, shiniest funk-synth numbers of the latter years of his career. Like a wine that grows on you slowly but surely, “Lavaux” has legs well beyond that first sip.