He is best known for his involvement with the Muppets, performing Miss Piggy, Fozzie Bear, Animal, and Sam Eagle for The Muppets Studio, as well as Sesame Street characters Bert, Grover, Oscar the Grouch, and Guy Smiley—all roles that he inherited from the characters' original performers, Frank Oz, Caroll Spinney, and Jim Henson.

[1][5] In 1992, while attending New York University's Tisch School of the Arts, he interned at the Jim Henson Company, working in the archival library.

[8][12] For the Muppets, Jacobson began performing Miss Piggy in 2001, debuting at the "MuppetFest" fan convention.

[13] The following year, he began performing Fozzie Bear and Animal, debuting in the roles in It's a Very Merry Muppet Christmas Movie.

[14] For Disney, Jacobson performed Harry the Duck on Bear in the Big Blue House and puppeteered Piglet on The Book of Pooh.