There is no shortage of adjectives to describe Mariah Carey and her longstanding career: iconic, tumultuous, unpredictable, diverse, groundbreaking, etc. We’re so far along into it now that we take certain things for granted, including Carey’s deep ties to and triumphs within the hip hop world, a space in which she didn’t always exist. Originally marketed as a pop artist set to compete with the likes of Madonna, it wasn’t until the release of her sixth studio album in 1997 that the hip hop world truly began to see the star as a cultural fixture.

Today (September 16) marks the 20th anniversary of Butterfly, which debuted at the top of the Billboard 200 in 1997 and went on to be certified five times platinum—no small feat.

To celebrate the anniversary of one of Carey’s most iconic albums, we’re highlighting the Elusive Chanteuse’s best hip hop moments, below.

Collaborating with Jay-Z
Imagine an alternate universe in which Jay-Z had stolen Mariah Carey’s heart instead of Beyoncé’s—actually, for some reason, that’s terrifying. So don’t. But we can see how the two vibe together on “Things That U Do,” a jam that also features production king Swizz Beats. Jay is but one of countless hip hop staples that Carey worked with while recording her fourteen studio albums, but likely remains the most relevant today.

Teaming up with Missy Elliott and Da Brat
While working on Butterfly, Carey decided to move away from working with Grammy award-winning songwriter and producer Walter Afanasieff to hit a more hip hop heavy sound. This led to her working with a plethora of other genre producers, including Missy Elliott, who you can hear alongside Da Brat in the “Heartbreaker” remix. While she spent much of her studio time working with men (the aforementioned Jay-Z was also a part of making this track), she certainly knew how to pick out the best of hip hop’s leading ladies.

Ties to Love & Hip Hop: Atlanta
Mariah Carey finally embraced reality TV (and we couldn’t be more thankful) in 2016 with the release of Mariah’s World. But she actually has ties to one of the most iconic hip hop oriented series of all time, Love & Hip Hop: Atlanta, through working with reality star Stevie J on “Honey” in 1997. The track became one of Carey’s most infamous, as well as an overt confirmation of her transition into the hip hop arena. It’s safe to say that the track, and thus Stevie J himself, are responsible for one of the most pivotal moments in Carey’s career.

The Story of Ol’ Dirty Bastard
While some report that Mariah Carey and O.D.B. feuded during their collaboration on the “Fantasy” remix, it seems like Carey wasn’t herself in the studio when it all went down. By “it” we mean a tantrum from O.D.B. that included his alleged threatening to kill a girl over the phone, demanding Moet and Newports, calling assistants “white devils,” throwing a bottle of Heineken on the floor, falling asleep three times and demanding an additional $15,000 when asked to record something over. Again, while Carey’s actual presence or involvement is up for debate, the woman was indirectly the catalyst to one of the genre’s most talked about diva breakdowns—and this time around, said moment didn’t belong to Carey.

Feud with Eminem
Mariah Carey has dated a lot of high profile men, but when she adamantly denied dating Eminem, Marshall Mathers didn’t take it well. The hip hop mogul sings a different tune, insisting that the two were romantically involved. “There’s truth to that” he told Rolling Stone in 2009 when asked about their relationship, and then went on to say: “But on the whole personal level, I’m not really feeling it. I just don’t like her as a person.” The beef gets played up in their music, mostly that of Mathers, who bites at her in songs like “Jimmy Crack Corn”, rapping, “Your minds on us like mine’s on Mariah / And y’all are just like her, you’re all f---ing liars.” The tension has only grown over the years and doesn’t seem to be going anywhere anytime soon.

Mariah Carey Gushing About Meeting the Fresh Prince
Back when she was only 18 years old, a relatively anonymous (read: not yet famous) Mariah Carey met Will Smith at the KISS FM Endless Summer Jam in Los Angeles in 1988. While this may not be what one might call an infamous hip hop moment in the performer’s career, her meeting the Fresh Prince back in the day made for an iconic photo—one which Carey posted on her Twitter with the caption, “#FBF I still can’t believe this picture…”

Daydream Album (1995)
While Butterfly officiated Mariah Carey as a hip hop star, the transition began subtly with her previous album, Daydream, in which she partnered up with the likes of producers Jermaine Dupri and Kenneth “Babyface” Edmonds in order to develop a more “urban” sound. The album also highlighted creative differences with her label and husband at the time, Tommy Mottola, who was heading Sony Music Entertainment and wanted to keep Carey boxed into the pop realm. The album was a success, leading to a whopping six nominations at the 38th annual Grammy Awards, despite Carey leaving empty-handed that night.

Working with Snoop Dogg
Few artists are as synonymous with “hip hop” as Snoop Dogg… which apparently is also synonymous with “Snoop” and “Snoop Lion” (it’s getting hard to keep track). When Mariah Carey paired up with the rapper for “Say Somethin’” in 2005, they also brought in Chad Hugo and Pharrell Williams, leading to one of the biggest singles on Carey’s 10th studio album, The Emancipation of Mimi. Not strange for Carey at that point in her career, the song is rather sultry, illustrating a man and woman discussing what they’d like to do to one another in a restroom.

Drama and Collaborating With Nicki Minaj
One of Mariah Carey’s most beloved qualities is her overt disdain for certain other celebrities. One very public example of this was captured when "Up Out My Face" collaborators Carey and rap queen Nicki Minaj were both tapped to judge the 12th season of American Idol. TMZ leaked a video of the two cursing each other out during auditions, in which one can hear Minaj saying, “I told them I’m not f*---ing putting up with your f---ing royal highness over there,” leading Carey to call the rapper a three-year-old. Rumor has it that Carey was putting Minaj down by saying that she can’t sing, although we can’t really be sure where this royal hip hop beef all started.

Marriage to Nick Cannon
While Nick Cannon’s resume lists a host of careers (actor, comedian, host, entrepreneur, etc.), he’s also well known for his imprint on the world of rap. Sure, he may not ring the same bell as the hip hop titans Carey’s been associated with in the past, but marrying a rapper does imply that hip hop is more than just Carey’s genre of choice—it’s also her lifestyle. While the two are (sadly, infamously) divorced at this point, the birth of Carey’s twins Moroccan Scott Cannon and Monroe Cannon will immortalize the hip hop power couple’s existence for years to come.

Frazer Harrison, Getty Images

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