The lead single from Mariah Carey's ill-conceived box office bomb, Glitter, "Loverboy," much like the 2001 film, was a hodgepodge of confusion both conceptually and musically.

That confusion was, sadly, carried over to the song's video—there was Cameo's Larry Blackman drag racing, Mariah Carey's face superimposed on hubcaps, very short shorts, and some pretty awful dancing.

It all pointed to a major life change for Carey, who during that year posted erratic messages on her website, made a memorable head-scratching, unplanned appearance on MTV's then-popular video show, TRL, and split from her record label, Columbia, in favor of Virgin Records for a five-album $100 million deal.

Years later, Carey revealed that she has bipolar disorder, and much of her behavior that year signaled to the emotional distress she was under during the time. By 2001 Carey was a megastar who was struggling to redefine herself as both an artist and a woman. When "Loverboy" was released, it was clear that she hadn't yet completely found her footing.

For what its worth, "Loverboy" still stands as one of Carey's most memorable videos, even if isn't necessarily for the best reasons. Let's look at the good, the bad and the ugly of "Loverboy."

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    • It sold well. Critics may have panned it as being clunky, unoriginal and contrived, but "Loverboy" was still the best-selling song of 2001 in the U.S. pointing to Carey's dominant star power.
    • The Cameo sample. You can't overstate the brilliance of funk group, Cameo. And anyone with the good sense to sample one of their best songs, "Candy," deserves props for trying.
    • Larry Blackmon drag-racing in the video. Why exactly is Cameo frontman, Larry Blackmon, drag racing Da Brat in the video? Who knows, but it's almost as impressive as that bright red crotch cup he refuses to retire.
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    • It was Carey's first commercial failure.  Yes, it was best selling single of 2001, but "Loverboy" was also Carey's first lead single that failed to hit No. 1 on the Billboard Hot 100. It peaked at no. 2, which at the time, was a significant blow for one of music's biggest pop stars.
    • Mariah Carey's dancing. Bless her heart, but Carey's rhythm is very questionable, and it's brought to light in this video, whenever she tries to dance sexily on a race track, on top of a car, in front of hubcaps— it's all pretty bad. If you notice, most of her unfortunate dancing shots are in slow motion, probably to help her catch the beat.
    • Glitter. Mariah Carey's romantic musical drama, Glitter has to be one of the most widely panned movies of the past two decades, alongside Jennifer Lopez and Ben Affleck's horrific, Gigli. Glitter was clowned relentlessly for its lack of quality, terrible acting and overall corny plot, becoming the butt of many pop culture jokes for years to come. Consequently, Carey found herself struggling to reclaim her star in a fickle industry that considered the film the beginning of the star's downfall. Of course, we now know that was far from the truth, as an invigorated Carey crafted what's considered to be her best album a few years later with 2005's creatively-fresh, career-defining release, The Emancipation of Mimi.

    • Beef with Jennifer Lopez and Tommy Mottola. Cue the Beastie's "Sabotage" for this one. Originally, Carey planned to sample Yellow Magic Orchestra's "Firecracker" for "Loverboy," but drama ensued after it was reported that her ex-husband, Tommy Mottola, and Jennifer Lopez stole the sample for the song, a full month after Carey had signed for it. Carey consequently changed the song's sample to Cameo's "Candy," and Mottola went on to use the stolen sample for J. Lo's hit single, "I'm Real" from her album, J. Lo. Talk about shade. Adding to the Glitter mess, Murder Inc. head, Irv Gotti, said that Mottola actually told him to create the Murder Remix of J. Lo's "I'm Real" to sound exactly like another Glitter song "If We," which featured Ja Rule and Nate Dogg. Could this be why Mariah Carey doesn't know J. Lo?
    • Erratic behavior. Leading up the release of Glitter, more controversy arose because of Carey's public, erratic behavior, which undoubtedly negatively impacted the reception of "Loverboy." She began posting concerning messages on her website including one that read, "I'm trying to understand things in life right now and so I really don't feel that I should be doing music right now..." She also made erratic TV appearances, including a surprise pop-up on MTV's TRL, in which she exhibited bizarre behavior— she came out pushing an ice cream cart and handing out ice cream bars, before performing a striptease. The appearance garnered a lot of attention, as did her erratic appearance at a Tower Music signing. Less than a week after "Loverboy" was released, she was hospitalized for severe mental and physical exhaustion.  As a result, Glitter was pushed back, and the soundtrack was delayed as well.
    • The soundtrack dropped on 9/11. An unfortunate coincidence, Glitter's soundtrack was released on Sept. 11, 2001, further adding to its disaster story.