Toni Braxton "Another Sad Love Song"

"Another Sad Love Song" played that March morning in 1998 when Toni Braxton walked onto the set of The Oprah Winfrey Show.  Braxton was on the show to discuss, among other things, her bankruptcy.  Having sold more than 20 million albums, no one could comprehend Braxton's money woes...including Oprah.  Oprah questioned Braxton's spending habits and accountability (Oprah couldn't comprehend why Braxton needed Gucci silverware).  During Braxton's Behind the Music episode on VH-1, Braxton discussed her interview with Oprah and claimed Oprah was "so frickin' mean" to her and the interview caused people to look down on her.  If you have a spare 18 minutes, take a look and see if Oprah was "so frickin' mean" or just showing her some tough love.  I'm gonna side with Oprah on this one...

Des'ree - "You Gotta Be"

Des'ree's "You Gotta Be" has been in countless movie and TV ads over the years, but the lyrics seem perfect for promoting The Oprah Winfrey Show.  Unfortunately, Good Morning America beat Oprah to the punch in 1995.