[9] His mother, Helene Stanton (née Eleanor Mae Stansbury; 1925–2017), was a singer and actress[10] who came from a "highly Victorian upper-middle-class family in Philadelphia".

"[15] In 1984, while still a medical student, Pinsky started appearing in "Ask a Surgeon", a segment of a Sunday night KROQ-FM show hosted by Jim "Poorman" Trenton and "Swedish" Egil Aalvik.

Loveline went national in 1995, and the television version launched on MTV the following year, hosted by Pinsky and Adam Carolla.

On November 27, 2007, Pinsky began Dr. Drew Live, another nationally syndicated talk radio show where he focused on a wider range of health issues.

On January 5, 2015, Pinsky launched a new weekday program, "Dr. Drew Midday Live with Mike Catherwood", on KABC in Los Angeles.

[25] Pinsky makes guest appearances on various news programs where he usually gives his observations on the relationship between controlled substances and high-profile individuals.

He has frequently given his views on the deaths of people such as Anna Nicole Smith, Heath Ledger and Michael Jackson, arguing that their fates should set examples of the seriousness of misusing drugs.

In early 2011, Pinsky began hosting his own show, Dr. Drew On Call on HLN that focuses on news involving health and addiction topics.

[42] In 2003, Pinsky authored Cracked: Putting Broken Lives Together Again, recounting his experiences as the medical director of the Department of Chemical Dependency Services at the Las Encinas Hospital drug rehabilitation clinic in Pasadena, California.

On September 10, 2020, it was announced that Dr. Drew Pinsky joined Aditx Therapeutics as Senior Advisor to AditxtScore for Scoring the Immune System.

[56] Between February and March 2020, Pinsky made a series of statements concerning the COVID-19 outbreak where he downplayed the seriousness of the pandemic, stating that it was not as bad as the flu, and suggested that it was a "press-induced panic".

[citation needed] Pinsky has raised concerns for several years regarding homelessness in Los Angeles County and has been critical of how the government has handled it, stating, "For some reason, the government has taken the position that this is a housing problem, which, of course, housing is a piece of this, but for most—and by most I mean the vast majority of people on the streets—their condition makes them unwilling or unwanting to go indoors.

"[59] He has also been critical of certain aspects of the Lanterman–Petris–Short Act, in that it limits the ability of authorities to intervene when mentally ill persons are at risk of death due to being unable to care for their own needs.

[59] Pinsky said in an interview that he had correctly predicted a typhus outbreak in 2019 that occurred in the county as a result of rodents attracted to homeless encampments.

[60] Critics claimed that Pinsky had overreported the number of homeless people with mental illnesses or substance abuse disorders.

[64] A transcript of this appearance and the invoice of the payment to Pinksy were later presented publicly as evidence during the criminal and civil actions against GlaxoSmithKline in 2012.

[65] In response to an inquiry from the Wall Street Journal about the case and specific physicians including Pinsky, the company declined to comment on their financial relationship with specific doctors, but acknowledged that "during the period from January 1999 to December 2003, there were some occasions on which certain GSK sales representatives, speakers, and consultants promoted its antidepressant Wellbutrin to physicians for uses which were not FDA-approved in violation of federal law.

Pinsky stated on the June 24, 2009, episode of Loveline that at one point, he was torn between practicing medicine and becoming a professional opera singer.

[76] Pinsky is a nonobservant Jew; he admits to abandoning most Jewish practices but claims to retain a continued desire to learn about the religion.

He explains that religious as well as philosophical studies affect his medical practice and his speeches, and that his background places "an indirect coloring on every answer.

[78] During episode 119 of his podcast Dr. Drew After Dark, aired on June 10, 2021, Pinsky said that his prostate cancer has recurred after it was discovered during routine bloodwork that his PSA (Prostate-specific antigen) level is elevated.

"[79] Politically, Pinsky considers himself libertarian, and has espoused more traditionally conservative views in recent years, such as the 'tyranny' of governmental overreach and the need for a "Liberty Party".