The song was written by the artists and produced by Carey and DJ Clue, with additional writers being credited for the hook being built around a sample from "Attack of the Name Game" by Stacy Lattisaw.

"Heartbreaker" received mixed reviews from music critics, many of whom felt it was not original or innovative in terms of a creative step forward.

The video features Carey and her friends visiting a film theater and catching her boyfriend (played by Jerry O'Connell) on a date with another woman.

With her sixth studio effort, Butterfly (1997), Carey started infusing hip hop elements in her songs, working with different, and younger, producers and songwriters.

[1] Her main focus on the album was to continue on the same path she began with on Butterfly, producing a subtle combination between inspirational ballads and hip hop beats.

"Heartbreaker" marked the first time in Carey's career that a rapper was included on a lead single, following Ol' Dirty Bastard, who was featured on the Bad Boy remix of "Fantasy" in 1995.

While recording the album in Capri, Italy, Carey claimed to have spent most of the time developing what she felt to be a strong lead single.

However, after completing "Heartbreaker", Carey felt it needed a strong male verse, hoping for a rising hip hop artist.

"[5] Aside from her work with Clue and Jay-Z, Carey's longtime friend and background singer Trey Lorenz also took part in the song's production.

[5] When interviewed by Bronson, Carey spoke highly of Lorenz, "He's an amazing writer and singer, he's so influenced by the old school stuff, yet he's so current.

"[5] Aside from the use of the sample and Jay-Z's verses, "Heartbreaker" contains strong female-empowering lyrics, which Carey wrote as a sort of anthem, especially because she felt that she personally has been in a similar predicament in the past.

"[6] Chuck Taylor from Billboard described its instrumentation as a "persistent guitar lick" and wrote "There's an identifiable chorus here, and some semblance of verses, but more than anything, this song comes across as a blur of jumbled voices in the background (à la Lauryn Hill), including Carey's own repetitive harmonies, which in this case sound more like a competition than a compliment.

It's also gonna go on the album, and it features Missy Elliott and Da Brat, and it's kinda like a girl-power answer record, and it's to the loop of Snoop [Dogg]'s 'Ain't No Fun.'

[11] Danyel Smith from Entertainment Weekly called it "[an] overblown [...] miscalculation" and wrote "Missy Elliott's and Da Brat's bad sexual politics sink the tired 'Heartbreaker [Remix].

"Heartbreaker" received mixed reviews from contemporary music critics, some of whom compared it heavily to Carey's previous lead singles.

[12] Elysa Gardner from the Los Angeles Times called the song "breezy" and noted how Carey "brings a similarly light, sensuous touch" to "Heartbreaker".

[5] The only acts still ahead of Carey were Elvis Presley with seventeen (a record she surpassed in 2008 with "Touch My Body" becoming her eighteenth number one single) and the Beatles with twenty.

[27] In New Zealand, "Heartbreaker" was met with strong success, debuting at number four on October 10, 1999, and topping the singles chart the following week.

It spent a total of eleven weeks fluctuating in the singles chart, and was certified platinum by the Recording Industry Association of New Zealand (RIANZ), denoting shipments of over 15,000 units.

[28] In the two Belgium territories, Wallonia and Flanders, the song peaked at numbers nine and twenty-seven, and spent nineteen and sixteen weeks on the chart, respectively.

[31] The song charted for twenty-five weeks, and was certified gold by the Syndicat National de l'Édition Phonographique (SNEP), denoting shipments of over 400,000 units.

Later, a version of the video was released where Jay-Z raps his verse in a Jacuzzi while Carey and a security guard appear behind, followed by segments of the animated film.

After she sits next to him and he notices who it is, Carey spills a large soda on his lap and bids him farewell, leaving the theater with her friends smiling.

Jay Z's voice (presumably her ex-boyfriend's internal dialogue, as it refers to the relationship in first person) explains that when they were a couple she was a very exploitative and controlling girlfriend, frequently demanding money and sex, using him to support her female cohorts and seeing him as some kind of trophy boyfriend.

She also frequently got into fights with other women if she believed he was being adulterous (oddly in concert with the video's live-action segments) and answering his phone to ensure he was not somehow cheating.

In order to promote "Heartbreaker", Carey performed the song live on several television and award show appearances, as well as recorded her own Fox Broadcasting Company special.

[40] Carey performed "Heartbreaker" and its accompanying remix at the MTV European Music Awards, held on November 11, 1999, in Dublin, Ireland.

[citation needed] During the tour, Carey wore a sparkling, Swarovski bikini number, and performed both the remix and original versions back-to-back.

[citation needed] For the song's recital, Carey's donned a black bikini and matching silk cape, as well as Christian Louboutin platform pumps.

[citation needed] For the show at Madison Square Garden in New York City, Carey was joined by both Da Brat and Jay-Z for the remix and original versions, respectively.