On April 22, 2009, Stryker announced that due to financial cutbacks at Westwood One, he would be leaving the show and it would be his last appearance that night.
After Stryker's departure, a number of celebrities guest co-hosted opposite Drew.
In 1984, Trenton added a segment called "Ask a Surgeon," hosted by his friend Drew Pinsky, who at the time, was a fourth-year medical student at the University of Southern California.
Furthermore, the comedy is often necessary to keep spirits high, as the show frequently handles callers who are dealing with serious issues such as drug addiction, sexual abuse, and domestic violence.
The show will occasionally answer calls of a general medical nature, especially on slow nights or if they seem peculiar.
Adam Carolla re-joined him as co-host for the final show. Loveline follows the call-in question-and-answer model with the primary goal of helping youth and young adults with relationship, sexuality, and drug addiction problems through the expertise of Pinsky, an internist and addiction medicine specialist, and the humorous context and insight provided by a comedic host.
On September 8, 2016, the show was rebooted as a weekly podcast, with Amber Rose and Dr. Adam Carolla explained his role as a "sheep in wolf's clothing".