Rocca was born in Washington, D.C. His mother immigrated there from Bogotá, Colombia, in 1956 at age 28, and his father was a third generation Italian-American from Leominster, Massachusetts.

[2] He served as president of Harvard's Hasty Pudding Theatricals, performing in four of the company's notorious burlesques and co-authoring one (Suede Expectations).

[3] While at Harvard, he also played Seymour in a production of Little Shop of Horrors which co-starred future Supreme Court Justice Ketanji Brown Jackson.

[4] Rocca appeared in the 2005 film Bewitched and, in 2007, in the independent science-fiction family comedy I'll Believe You with fellow Daily Show alumnus Ed Helms.

In 2012, Rocca was the narrator of the documentary Electoral Dysfunction, a movie which satirically analyzes the American voting system and which aired on PBS in 2012 and 2016.

He is also the host of the weekly The Henry Ford's Innovation Nation program, which has aired as part of the CBS Dream Team on Saturdays since 2014.

[11] During both times on the show, he played in support of the Inner-City Scholarship Fund, a New York-based charity that helps low-income families enroll their children in Catholic Schools through financial aid.

Rocca began his career acting on stage in the Southeast Asia tour of the musical Grease (1993) and Paper Mill Playhouse's South Pacific (1994).

On Broadway, Rocca played the role of Vice Principal Douglas Panch in The 25th Annual Putnam County Spelling Bee.

[15][16] In February 2024, he announced that Roctogenarians, a Mobituaries-style book focusing on people who achieved success late in their lives, would be released in June.

[19] On September 25, 2015, Rocca served as Lector during the Mass celebrated by Pope Francis at New York City's Madison Square Garden, giving a reading in Spanish.