Playlist: The Very Best of Michael Bolton features 14 tracks (and one CD-R track) defined on the back jacket as "the life-changing songs, the out of print tracks, the hits, the fan favorites everyone loves, and the songs that make the artists who they are." In Bolton's case, that sentiment rings mostly true, as it capably condenses the far more comprehensive, two-disc Essential Michael Bolton collection into a digestible morsel. There are enough Bolton classics like "When a Man Loves a Woman" and "How Am I Supposed to Live Without You" to ring true with casual fans, but longtime listeners who have followed the man since his golden-maned heyday will want more than just the meat off of the bone.