"Playlist: The Very Best of Toni Braxton" is the fourth greatest hits compilation released by Braxton, following "The Essential Toni Braxton, in 2007. The album was released on October 28, 2008, by Legacy Recordings, being part of Sony BMG's Playlist series. The tracklist contains Braxton most successful singles, with a few different tracks, such as "A Better Man" from her fourth studio album, "More Than a Woman" (2002), "Maybe", a single from "The Heat" and an Hex Hector remix for "Spanish Guitar". Enhanced section includes the interactive digital booklet with liner notes, photos and more.

Most modern-day female pop singers start their careers doing their sexy, stylish dance-oriented material then settle into a career as an adult contemporary crooner. Toni Braxton didn't follow that route. She started the '90s singing elegant, refined quiet storm ballads and ended it singing sleek dance-pop tunes as she slinked around in skimpy outfits. She wasn't the only one of her peers to follow this trajectory – Mariah Carey pretty much did the same thing, only to the extreme – but it's a little odd to listen to Braxton evolve from the sophisticated urban contemporary crooner to oversexed R&B thrush, even if it's not a bad thing at all. One thing that elevated Braxton above her peers is that she was a controlled, powerful singer who rarely oversang, and she had a good selection of material, much of it written or co-written by Babyface. That's why her 18-track hits collection Ultimate Toni Braxton works well even through her shifts in style – she is a confident enough performer to sell both the slow romantic ballads and material that swings harder.

Toni Braxton went through a lot in the years separating her star-making Toni Braxton and her 2000 comeback The Heat. Yes, she became a star, but she also went through a painful bankruptcy that delayed her sequel for years. Fortunately, you wouldn't be able to tell that there was so much behind-the-scenes drama from The Heat – it's a confident, assured, sexy effort that reaffirms Braxton's status as one of the finest contemporary mainstream soul singers. She may not be as street-smart as Mary J. Blige, nor does she push the boundaries of the genre the way TLC does, but she has a full, rich voice that instantly lends her songs a sense of maturity and sensuality, especially since she never, ever oversings or misjudges her material.