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Jacobson initially started playing Bert in 1997, but officially joined the cast as Bert and additional Muppets in 2000. His role expanded in 2002 to include new Grover segments, particularly Global Grover. In 2001 he and David Rudman played Cookie Monster until 2002 when Sesame Workshop chose David as Cookie so there would be more interaction between Bert, Grover and Cookie Monster. However, Oz occasionally comes in to record new material with those characters.
His second role came in 2001 with The Book of Pooh, where he worked on Piglet and Kanga. That year, he also began playing Miss Piggy, debuting at the "Muppetfest" convention. Subsequently, in It's a Very Merry Muppet Christmas Movie (2002), he performed the roles of Miss Piggy, Fozzie Bear and Animal. In The Muppets' Wizard of Oz (2005), as well as Sam the Eagle.
Jacobson appeared as the Little Bad Wolf in the pilot episode of Jack's Big Music Show.
- The Muppets - Miss Piggy (2001 – present), Fozzie Bear (2002 – present), Animal (2002 – present), Sam the Eagle (2005 – present), Marvin Suggs (2011 – present)
- Sesame Street - Bert (1997 – present), Grover (1998 – present), Cookie Monster (2002, 2005) and Guy Smiley (2005 – present)
- Play With Me Sesame - Bert & Grover
- Bear in the Big Blue House - Harry the Duck
Jacobson's Miss Piggy has appeared on Rove Live, Live with Regis and Kelly, The Tony Danza Show, Good Morning America, This Morning. and appeared in an episode in theDisney Channel Original Series So Random.
His Grover has appeared on Good Morning Australia, Rove Live, and Jimmy Kimmel Live!. His Fozzie has appeared on Saturday Night Live, Jimmy Kimmel Live!, and The Late Late Show with Craig Ferguson. Extreme Makeover: Home Edition included Muppet guests, such as Jacobson's Miss Piggy, Fozzie Bear, and Animal. Jacobson's Bert appeared in episode 22 of Between the Lions' season 2, "Tweet! Tweet!".