She is also known for her recurring role as Judy Geller on the NBC sitcom Friends (1994, 1996–2003), for which she was nominated for the 1995 Primetime Emmy Award for Outstanding Guest Actress in a Comedy Series.

Pickles appeared in Broadway plays in the 1960s and 1970s, including The Misanthrope (1968) and Sherlock Holmes (1975), and starred on the daytime soap operas Guiding Light (1970–1972, 2007) and Another World (1977–1979).

[4] She began attending the Royal Academy of Dramatic Art in London at age 14 and studied alongside Albert Finney, Peter O’Toole, and Brian Bedford.

After moving from New York City to Los Angeles, Pickles was cast as Nurse Helen Rosenthal in the NBC medical drama St.

Pickles has appeared in many films, including Masters of the Universe (1987), Revenge of the Nerds IV: Nerds in Love (1994), Legends of the Fall (1994) directed by Edward Zwick, Grace of My Heart (1996), Baz Luhrmann's Romeo + Juliet (1996), The Wedding Singer (1998), Sol Goode (2003), George of the Jungle 2 (2003), and Atlas Shrugged: Part I (2011).

In the 2000s, Pickles appeared in a few episodes of How I Met Your Mother as Lily Aldrin's grandmother, and guest-starred on The Division, Medium, and Childrens Hospital.

In 2016, she was cast in the ABC drama pilot The Death Of Eva Sofia Valdez, starring Gina Torres in a title role.