According to college friend Gary Lucas, a guitarist who went on to collaborate with avant-garde acts like Captain Beefheart, at Yale in the early 1970s he fell in with "lunatic fringe types and free thinkers".

Bill Moseley, another college friend who went on to a career in horror movies like Texas Chainsaw Massacre 2, stated, "I think of him as an artist first and foremost".

[9] After school, he worked at a Sonoma vineyard winery and then took a job in New York City as a commercial banker in Citibank's shipping lending unit.

In 1995 he became CEO of HBO, in which capacity he tripled company profits and "oversaw a fundamental shift in its content, away from just movies and fights and toward original shows like The Sopranos".

In January 2006, Bewkes and CBS Corporation head Les Moonves helped broker the deal that joined the CBS-owned UPN with The WB to form The CW Network.

Within a decade Bewkes' modus operandi "has been torched and replaced by Netflix’s subscription-based streaming model", costing Time Warner shareholders billions of dollars in the process.