His other notable lead credits include Loser (2000), Saving Silverman (2001), Anything Else (2003), My Best Friend's Girl (2008), Life Happens (2011), Grassroots (2012), and Best.

In television, Biggs is known for his lead roles as the voice of Leonardo in Teenage Mutant Ninja Turtles (2012–2014) and Larry Bloom in the Netflix original series Orange Is the New Black (2013–2014; 2017; 2019).

His other television lead credits include Drexell's Class (1991–1992), Total Security (1997), Mad Love (2011), and Outmatched (2020).

In 1988, aged 10, he received his Screen Actors Guild card for appearing in a TV commercial for Pathmark.

He also starred (along with his Loser co-star Mena Suvari) in the music video for the song "Teenage Dirtbag" by American rock band Wheatus.

He appeared in the 2002 Broadway production of The Graduate as Benjamin Braddock alongside Kathleen Turner and Alicia Silverstone.

In 2006, Biggs was seen in the MTV reality show Blowin' Up with Jamie Kennedy and Stu Stone which led to his participation in a hip-hop recording with Bay Area rapper E-40.

In 2010, Biggs made his literary debut by contributing "Scratch-and-Sniff", a poem about growing up in New Jersey, to the anthology What's Your Exit?

In the summer of 2012, Biggs took a job voicing Leonardo on Nickelodeon in Teenage Mutant Ninja Turtles.

[14] Seth Green permanently took over the role from Biggs beginning in season 3, with Leonardo's voice change being explained in the show's universe, as it was due to his throat getting injured in a battle against Shredder.

In December 2014, The Hollywood Reporter announced Biggs was cast to star in the comedy Amateur Night.

Biggs plays a well-meaning expectant father who unwittingly accepts a job chauffeuring prostitutes (Janet Montgomery, Ashley Tisdale) around Los Angeles.

[24][25] Biggs and Mollen sold their house in Los Angeles, California, which was situated near the Sunset Strip, in 2015[26] and moved to Manhattan, New York City.

[31][32] In a 2012 interview, Biggs stated that he has "a very fucked up sense of humor" and said he enjoyed the ability to "surprise people on a daily basis" on Twitter because his real personality is so different from those of the characters he usually plays.