He later achieved success in two popular musicals, Ragtime (1998) and the 2003 revival of Gypsy as "Herbie" opposite Bernadette Peters.

He was reunited with his Gypsy co-star Peters in a one-night-only benefit reading of Love Letters in September 2007, for Opening Act.

[4] Dossett appeared in the world premiere of the Michael John LaChiusa and Sybille Pearson musical Giant, as Bawley, at the Signature Theatre in Arlington, Virginia through May 31, 2009.

[6] He played the role of "Aaron" in the new musical First Wives Club, starting in July 2009 at the Old Globe, San Diego, California.

[8][9] In September 2011, he played the role of Joseph Pulitzer in the premiere of the Disney stage musical Newsies at the Paper Mill Playhouse in Millburn, New Jersey.

[14] He played the role of "Larry Murphy" in the Off-Broadway production of Dear Evan Hansen, which opened in previews on March 26, 2016, at the Second Stage Theatre, and closed on May 29, 2016.