In his nearly four decades as a recording artist, Prince was no stranger to controversy. In fact, “Controversy” was the name of his fourth album. But when Prince stoked the fires of public controversy in the media with his music, it was usually for one reason, and one reason only: Prince was just being too damn naughty.

Filmmaker Kevin Smith once described Prince thusly: “He’s always had one foot in the corporeal, and one foot in the spiritual.” Songs like “I Would Die 4 U” and “The Ladder” were clearly about religion and spirituality, but then the other half of his musical library was usually about sex. And not just sexy in a “Barry White slow jams” kind of way—although he did that too—but often in an explicit way that America had never heard before from a mainstream pop artist. He went there.

But more often than than not, these were some of Prince’s best songs, and the most beloved among fans. Here are but 10 of Prince’s most racy and controversial songs, the ones which earned him the nickname “His Royal Badness.”

1. Head (1980)

Although Prince certainly had sexy songs on his first two albums, it was his 1980 album Dirty Mind that solidified him as the most sexually provocative pop artist of his day. A perfect example of why would be the album’s sixth track, “Head.” And yes, the song is about exactly what the name suggests it is.

The song’s narrative has Prince meeting an 18-year-old woman on the way to her wedding; he seduces her away from her upcoming nuptials with the promise of great oral sex. The woman in question is played in a spoken word portion of the song by Lisa Coleman, future half of the duo Wendy & Lisa.

A little addendum to this song: In the wake of Prince’s death, news coverage on CNN had anchor Don Lemon and other anchors/pundits talking about which was their favorite song from the late singer—most said the usual top 10 hits. Don Lemon however, sheephishly admitted his favorite Prince song was “Head,” much to the shock of the other panelists. You are now my favorite news anchor ever, Mr. Lemon.

2. Sister (1980)

Maybe the most upbeat and catchy song about incest ever recorded, “Sister” is another song from Prince’s Dirty Mind album. In the song, the lyrics include “I was only sixteen but I guess that’s no excuse / My sister was thirty-two, lovely, and loose,” and “My sister never made love to anyone else but me / She’s the reason for my, uh, sexuality.” The song concludes with Prince begging his sister to not put him out on the street again.

For years, fans have wondered if there was any truth to this song. The answer is… there sort of might be? Although the truth might be icky, it’s probably not quite as icky as the song suggests. When Prince’s mother remarried, her new husband had a grown daughter that became Prince’s new stepsister. At the age of 16, Prince went to New York and lived with her for a brief time, until she kicked him out, leading fans to speculate that “Sister” was all about her. If true, Prince took something that was dirty and wrong, and then made a song about it that was somehow even filthier. God bless ‘im.

3. Jack U Off (1981)

This playful little ditty was the closer to his 1981 album Controversy, and like “Head” before it, is about exactly what the title suggests. Although never released as a single, this song is notorious for an incident that might have ended a lesser artist’s career. Despite just being a cult act with one radio hit to his name at the time, the Rolling Stones asked Prince to play as opening act for their show in Los Angeles. He would be playing to the biggest crowds of his whole career.

When Prince showed up on stage in bikini briefs, heels and a trenchcoat, the mostly white, male, classic rock-loving audience didn’t know what to make of him. When he busted out “Jack U Off,” the audience freaked out and started yelling homophobic slurs and throwing everything in sight at the stage, forcing Prince and the band off before their set was done.

The song was only unintentionally homoerotic, and was actually written about a woman, but Prince’s bassist Mark Brown later said “when you talk about street lingo, where I come from, guys don’t jack girls off. I don’t think Prince understood that—Prince was in his own world.” After the incident, concert promoter Bill Graham came out and chastised the audience, telling them they would all pay good money to see Prince in several years. He was wrong—within just a one year, Prince would be one of the biggest stars on the planet.

4. Nasty Girl (1982)

Although technically not a Prince track, he wrote, produced, and is actually heard giving his signature high pitched scream at the end of the song, so I say it counts. This track was released as the first single for Vanity 6, Prince’s pet project for his then girlfreind Vanity. Vanity was actually Denise Matthews, a model/singer Prince met at the American Music Awards who he saw as “the female version of himself.” He wanted to change her name to Vagina (pronounced Vah-Geena) but of course, the record label wouldn’t have it, so they settled on the name Vanity.

The song has displays Vanity as an brazenly sexual machine, who’s “lookin’ for a man to love her/Like she’s never been loved before.” While it wasn’t unusual to find love songs sung by women, it was nearly impossible, in our “slut shaming” culture, to have powerful women sing “lust songs” on pop radio. Vanity came out in the video for this song, dressed in lingerie, a full two years before Madonna’s Like A Virgin, claiming that she “can’t control it…” and that she “needs seven inches or more.”

Although this song was a #1 hit on the dance charts, it would be Vanity 6’s last. After a brief and tumultuous relationship, Prince and Vanity would break up, and he would fire her from her own group and replace her with Apollonia, a shameless lookalike/soundalike. But Vanity and Prince would lead eerily similar lives: both would find religion later in life, both would change their names to make a break with their past selves, and sadly, both would die within weeks of each other, both at the age of 57.

5. Erotic City (1984)

This song is a testament to just how huge Prince was in the wake of Purple Rain. That album had launched four top 10 hits—two of which went to #1—and the radio was desperate for new catchy Prince tunes to play. They found one on the B-side to “Let’s Go Crazy” with “Erotic City,” a duet between him and his protege/bandmate/girlfriend Sheila E.

Technically, the lyrics are said to say “We can FUNK until the dawn/making love till cherry’s gone.” But no one believed he said “Funk,” including the FCC, who levied fines against radio stations in Texas, Arizona, and Nevada for broadcasting allegedly indecent material. But radio kept playing it anyway, and “Erotic City” was that song you used to crank up whenever it came on…unless your parents were walking by the door, in which case you lowered it so you wouldn’t get in trouble.

6. Darling Nikki (1984)

Arguably the most famous of Prince’s highly sexually charged songs, if only because of its inclusion on Purple Rain, and the Prince album that even the most casual fans had in their collection. The song tells the story of a “sex fiend” named Nikki who seduces Prince when he catches her masturbating with a magazine in a hotel lobby. (Prince’s sexual imagination is nothing if not interesting.) This is one of Prince’s most eclectic songs, equal parts hard rock and funk.

Of course, the other reason this song has such notoriety is because of rumors that Al Gore’s wife Tipper Gore co-founded the Parents Music Resource Center (PMRC) in 1985 after she witnessed her 11-year-old daughter listening to this song. The PMRC eventually led to the use of “Parental Advisory” stickers and imprints on album covers. Hey, you know what, Tipper? I was an 11-year-old who listened to this song over and over. And I turned out just fine, thank you.

Actually, on second thought, maybe Tipper had a point.

7. Sugar Walls (1985)

In the early ’80s, Sheena Easton was a Scottish pop singer best known for such wholesome Top 40 hit songs as “9 to 5 (Morning Train)” and “Telephone.” For proper context, these are the kind of pop songs your mom would have loved and approved of. Then Prince got a hold of her, and things…got less wholesome.

Prince wrote and produced a new song for her album called “Sugar Walls,” under the pseudonym “Alexander Nevermind.” In case you had any doubt, yes, “sugar walls” is indeed a reference to her vagina. The song is anything but subtle about it, with lyrics like “temperatures rise inside my sugar walls/heaven on Earth inside my sugar walls,” etc.

Prince calling up Sheena Easton to tell her he’d written a song for her about her vagina he’d just love to produce, well… that’s a conversation I would have loved to eavesdrop on. In any event, “Sugar Walls” was a hit, reaching the top 10 in the U.S., incurring the wrath of both Tipper Gore (again) and televangelist Jimmy Swaggart. Sheena Easton would stay in Prince’s circle for while, appearing on his hit 1987 single “U Got the Look.”

8. Gett Off (1991)

By the time that “Gett Off” came out in 1991, a song about “32 positions in a one night stand” wasn’t nearly as racy as it would have been just 10 years earlier, in large part to Prince paving the way for highly sexualized content on the pop airwaves.

But maybe the most notorious thing about “Gett Off” wasn’t the song, but the performance that accompanied it at that year’s MTV Video Music Awards. Prince performed the song in a fitted banana-yellow outfit with assless pants. When he turned around and showed off his naked bum to the world, it was the talk of every single human being with cable access. Interestingly, the assless pants thing only helped his career, and the corresponding album Diamonds and Pearls was one of the biggest hits of Prince’s life, just beneath Purple Rain and Batman.

Side note: Interesting that Janet Jackson exposed her breast for a brief second a decade later on live TV, and it essentially killed her career dead in its tracks, while Prince can show off his ass on national TV and just get more popular. But there’s no sexism in our culture, right?

9. Sexy MF (1992)

Maybe the last really racy single Prince ever release that charted commercially was “Sexy MF”—which was edited as simply “Sexy Mutha” for the radio. The song was a precursor to a decade of hip hop numbers that would relegate to a series of bleeped out obscenities. After this song, Prince would get less and less sexually explicit in his lyrics, and by the year 2001, he’d convert to the Jehovah’s Witness religion, which didn’t allow him to use explicit language in his songs anymore, or even in everyday speech. “Sexy MF” was, in a way, the end of an era.

10. Orgasm (1994)

Most people don’t know this song, unless they’re really hardcore Prince fans. It’s off the album “Come,” which was released amidst the legal battle between Prince and his-then label Warner Bros. As such, the album was barely promoted, and was seen as a throwaway. The album’s final track “Orgasm” is basically guitar wails, the sound of crashing waves on a beach, and a woman having an orgasm while Prince goads her on.

Legend has it that the orgasm in question was real, recorded by Prince during a “session” with a mysterious lady friend. In the album liner notes, he credits the woman in the song as “she knows.”  Could it be Vanity? Appollonia? Sheila E? Madonna? Kim Basinger? Carmen Electra?? The fact that there are no shortage of famous women it could be has kept fans guessing for years, and that alone is what makes this song more controversial more than anything else.

With so many controversial Prince songs to choose from, which others do you think we should have included? Let us know your thoughts in the comments below.

Images: Warner Bros.