Born in Brooklyn, Portnow was so determined to break into show business that he eventually graduated from Brooklyn College with a degree in speech and drama. Though he performed early and often at Cafe La Mama, an experimental theater in the East Village, among other venues, his screen career didn't begin until 1980, when he made his film debut as a homeless drunk in the musical comedy "Roadie." After landing a recurring role as a squad captain on "The Equalizer," Portnow briefly appeared in Woody Allen's "Radio Days" (1987) before portraying a hard-up salesman in "Tin Men." That same year Portnow was re-cast as radio announcer Dan 'The Man' Levitan in "Good Morning, Vietnam." A small but memorable role as a chop shop owner in Arnold Schwarzenegger's hit comedy "Twins" (1988) followed by a turn as a no-nonsense IRS agent in "Say Anything. ." capped off a string of roles that proved to be a huge break for the still-unknown actor.The next decade saw Portnow appearring in increasingly high-profile projects. He portrayed a surly police captain in the smash hit "Kindergarten Cop" (1990), and continued his streak of authority figures by playing a detective in the Coen Brothers' odd thriller "Barton Fink" (1991). In 1993 he landed a feature role on the short-lived ABC sitcom "Home Free," which starred a pre-Chandler Bing Matthew Perry, and worked steadily until landing a cameo role as a hardened doctor in David Fincher's disturbing crime film "Se7en." Just a year later, Portnow was offered another series role, this time on the critically-acclaimed Canadian cop drama "EZ Streets," which he followed with a stand-out performance as radio shockjock Howard Stern's father in Stern's autobiographical 1997 film "Private Parts." The year 1999 was memorable for many reasons (Y2K, anyone?), but for Portnow it marked the beginning of one of his best-known roles: tough-as-nails Mob lawyer Harold "Mel" Melvoin on the groundbreaking drama "The Sopranos." A series regular on the influential series from 1999 to 2004, Portnow also starred as a doomed Mob boss in Jim Jarmusch's "Ghost Dog: The Way of the Samurai" (1999) and branched out into voice acting with a role as Beast in the "X-Men 2" tie-in video game "X2: Wolverine's Revenge" (2003). Portnow next appeared as a tough-talking judge in several episodes of the David E. Kelly series "Boston Legal," and directed the short film "In Pursuit of Woody Allen" (2007). In 2009 he was featured as a defense attorney in the ho-hum Jamie Foxx thriller "Law Abiding Citizen," and was later cast as Paramount president Barney Balaban in the underwhelming 2012 biopic "Hitchcock."