With Britney Spears poised to debut at #1 next week with her new single, “Hold It Against Me,” it should be noted that the pop star is not immune from delivering the occasional clunker.

Britney’s 2004 cover of Bobby Brown’s “My Prerogative,” for instance, which served as the title track and lead single for her first greatest hits set was one of her biggest misses. Though the compilation did well, her version of “My Prerogative” landed with a particularly loud thud, not even breaking the Billboard Hot 100.

I can understand why those in Britney’s circle felt a re-do of Brown’s assertive anthem was the right fit. She was battling the media at the time, with her personal issues only beginning to reveal themselves (two marriages, a mess of a reality show). Brown, who, like Britney, had found himself the focus of unwanted attention and had to face troubles of his own, conceived “My Prerogative” as an answer to carping critics. But unlike Britney, he took the song to the summit.

“My Prerogative” was the last song written and recorded for Brown’s second solo album, Don’t Be Cruel (yep, there was one before it). Musically, the former member of New Edition had the final word — at least for a hot minute — selling 8 million copies of the album and notching five top ten hits, including “My Prerogative,” which reached #1 on January 14, 1989, 22 years ago this week:

Purchase Bobby Brown – “My Prerogative” via iTunes, Amazon MP3.