Skybell grew up in Lubbock, Texas, and performed in two productions of Fiddler on the Roof from an early age: First as a "chuppa boy" and then Tevye at the Interlochen Center for the Arts summer camp.
He went on to attend the Yale School of Drama, performing alongside Jodie Foster in Getting Out, directed by Tina Landau.
[3] Skybell worked with Stephen Schwartz and Joe Mantello on the workshop for Wicked,[4] playing the character Doctor Dillamond.
He starred as Tevye in the all-Yiddish production, directed by Joel Grey, Fidler Afn Dakh at the Museum of Jewish Heritage by National Yiddish Theatre Folksbiene.
In 2024, Skybell played Herr Schultz in Cabaret at the Kit Kat Club, opposite Bebe Neuwirth as Fraulein Schneider.