In 1998, their fourth album, Dearest Christian, I'm So Very Sorry For Bringing You Here, Love Dad was less successful again, with the album's single, "Being So Not For You (I Had No Right)" being only a minor chart hit.
In 2000, they released a greatest hits album, The Best of P.M. Dawn, a release of previous tracks plus new singles.
In June 2005, P.M. Dawn won the fifth round of NBC's hit TV show Hit Me Baby One More Time, performing "Set Adrift On Memory Bliss", and covered Puddle of Mudd's "Blurry", designating their $20,000 charitable prize to go to Child Diabetes research.
2005 also marked the year of some major changes within P.M. Dawn. Member (and brother) J.C. decided to leave P.M. Dawn to pursue an interest in a solo career. This led to the introduction of Doc.G, who is also family (paternal first cousin).
In June 2006, P.M. Dawn commenced a summer tour called "Summer of Bliss, 2006.", playing venues across the United States in an effort to promote a new album, P.M. Dawn Loves You which was to be released in 2007 with a live album also expected to be recorded that year. As of November 2008 neither album has been released.