Rifkin has enjoyed a long and distinguished career in film, on stage, and in television. His association with writer Jon Robin Baitz has been especially fruitful. In 1991, his performance in Baitz’s play The Substance of Fire won him the Obie, Drama Desk, Lucille Lortel, and Drama-Logue awards for Best Actor. The following year, he performed in Baitz’s Three Hotels, for which he received a second Lucille Lortel and Drama Desk nomination. In 1996, he starred in the film version of Substance; in 2002, he appeared in the Baitz play Ten Unknowns at Boston’s Huntington Theatre; in 2004, he starred in his play The Paris Letter at the Kirk Douglas Theatre in Los Angeles, a role he reprised the following year at the Laura Pels Theatre in New York City; and appeared in the ABC drama series Brothers & Sisters, which Baitz created, as a character named Saul, Rifkin’s real-life name.

In 2001, his association with Touchstone Television began when he played a ruthless intelligence agent Arvin Sloane in Alias, opposite Jennifer Garner. Until 2011, he played second-in-command businessman Saul Holden on Brothers & Sisters, opposite Sally Field. He also played Bonnie Franklin’s second boyfriend on One Day at a Time.

On October 1, 2020 a video was uploaded on Christian Coppola’s YouTube channel where he starred as Mr. Smith in a short film called “Daddy” alongside Dylan Sprouse who played Paul. The film entails: “after the death of his wife, an 80-year-old man checks into The Plaza Hotel to celebrate their first anniversary apart, hiring a male escort to take her place.”