During his last year in medical school, Pinsky signed on to work as the co-host of a local, late-night radio show called Loveline on 106.7 KROQ FM. The then-unknown love advice show launched in 1983 with hosts DJ Jim "Poorman" Trenton and DJ Swedish Egil (Egil Aalvik). After a year, the show added a segment called "Ask a Surgeon" for which Trenton recruited his friend, Pinsky, to give medical-related advice. Soon, the segment became part of the show, and Trenton and Pinsky were made co-hosts.
In 1992, the show, which now broadcasts throughout the U.S., Canada, and Mexico, was given the green light to air Sunday through Thursday from 10:00 p.m. to midnight rather than during its usual Sunday evening time slot. MTV VJ Riki Rachtman replaced Trenton on the show in 1993. The show was granted national syndication in 1995, just as another host, comedian Adam Carolla, was added. When Rachtman and Carolla butted heads while competing for airtime the following year, Rachtman decided to leave the show.
For the next 10 years, Pinsky and Carolla nurtured a listener following with their impeccable on-air chemistry. With listeners calling in with relevant, and sometimes bizarre, sex and relationship questions, Pinsky and Carolla helped create an entertaining and informative show that teenagers and adults alike could enjoy and learn from. Pinsky's conservative and book-smart persona contrasted with and complemented Carolla's raw and witty humor.
During these years, the team began hosting speaking tours and making cameos on television and in films. From 1996 to 2000, MTV made the radio show into a live television show with a studio audience. They also released a book in 1998 called The Dr. Drew and Adam Book: A Survival Guide to Life and Love.
By 2005, the duo had achieved celebrity status, and Carolla opted to leave the show for other projects. While the show struggled to find a replacement for Carolla, Pinsky continued hosting the show with various celebrities and guests. Finally, in July of last year, the radio station's DJ Stryker took the vacant co-host spot, and he has been hosting ever since.
After he graduated from medical school, Pinsky did his residency at Huntington Memorial Hospital in Pasadena. Eventually, Pinsky earned a position as chief resident at a USC facility, Huntington Memorial Hospital. As a board-certified internist and addictionologist, Dr. Drew is also the medical director of the Department of Chemical Dependency Services at Pasadena's Las Encinas Hospital and the chief of service in the Department of Medicine. Dr. Drew is also the past president of the Pasadena Medical Society and the former editor of the Los Angeles County Medical Association magazine.
In addition to hosting Loveline five nights a week, Pinsky is also an assistant clinical professor of psychiatry at his alma mater, Keck USC School of Medicine, and an active staff member at Huntington Memorial Hospital in Pasadena.