Ariana Grande’s forthcoming album Dangerous Woman boasts a lot of big names in the features column. Nicki Minaj, Future, and Lil Wayne all supply verses to her third LP, but one guest stands out in particular: Macy Gray, the Grammy-winning singer of the 1999 hit “I Try."

Gray’s biggest single is now more than 16 years old, and she hasn’t made too many guest appearances on big name pop albums like Dangerous Woman. But if you listened to the radio at all around 1999 and 2000, her voice is seared into your formative memories. Her gravely rasp was unmistakable against the late ‘90s backdrop of boy bands and R&B, both of which prioritized almost impossibly smooth singing. On “Leave Me Lonely," she’s the perfect foil; her voice stands jagged in sharp contrast to Grande's silky glissando.

“Dangerous love, you’re no good for me, darling,” Gray sings on Grande's latest song. She had similar concerns back in 1999, when she worried about the “games, changes, and fears” that plagued her love in “I Try.” That kind of fraught obsession fills Dangerous Woman, which so far has left behind the romantic self-assuredness of Grande’s 2014 single “Problem.” Grande isn’t in a position to flick exes away like stray bugs now. She’s stuck in the “is you is or is you ain’t” limbo, whether she’s using that ambiguity to seduce (“Let Me Love You”) or embracing optimism in the midst of uncertainty (“Be Alright”).

“Leave Me Lonely” squares desire with self-preservation like “I Try” did, but here Gray and Grande both opt for the latter. Instead of falling down and choking on a love that just won’t work, they swallow their pride and move on.