[citation needed] While Siegel was student teaching at Oneonta University, a professor who was amused by his classes, directed him towards show business.

[citation needed] On the show with Siegel were co-hosts Billy Costa and Lisa Donovan,[4] and producers Justin Aguirre, Winnie Akoury and Dominick Famularo.

Although Siegel was best known for his comedic and light-hearted approach to morning radio, two of his most memorable shows came in the wake of tragedy: September 11th and the Boston Marathon Bombings.

During both instances, Siegel stayed on the air all day providing critical updates and a calm presence to his Boston listeners.

[5] At approximately 9:20 a.m. on May 19, 2021, Siegel announced on air that his bosses had ordered him to stop discussing the news of Demi Lovato coming out as non-binary and ended the broadcast abruptly with the words "Matty out.

[13] As host of Matty In The Morning, Siegel won the National Association of Broadcasters' Marconi Award for Personality of the Year (major market) in 2001[14] and 2009.