He went on to appear in the premier of David Mamet's November with Nathan Lane and Laurie Metcalf at the Ethel Barrymore Theater and performed it once more with John Malkovich and Patti Lupone for Stars in the House.

More recently Phillips played leading roles in the premiers of Dennis Kelly’s Taking Care of Baby, Terrence McNally's Golden Age, and Sharyn Rothstein's By the Water, all for the Manhattan Theatre Club (off-Broadway).

Most recently, Phillips played Murray Lefkowitz in the Broadway premier of Ayad Akhtar's Junk: The Golden Age of Debt at Lincoln Center's Vivian Beaumont Theater.

Other features include For Richer or Poorer, Jeffrey, The Shadow, Wagons East, The Man Without a Face, Green Card, Lean On Me, Critters, Bloodhounds of Broadway, The Island, Bad Santa, and The Babysitters.

His more recent films include Shadow Witness, Audrey, the Coen Brothers' Inside Llewyn Davis, Woody Allen's Irrational Man, and James DeMonaco's The Purge: Election Year.

He has made scores of guest appearances on television series and tele films, including Pushing Daisies, Bones, Eli Stone, Criminal Minds, NUMB3RS, Las Vegas, L.A. Law, JAG, Law & Order, Arrested Development, Boston Legal, Touched by an Angel, Castle, Rizzoli & Isles, The Good Guys, The Mentalist, Deadbeat, The Good Wife, New Amsterdam (2018 TV series), Better Call Saul and Veep.