After receiving his Bachelor’s Degree in Theatre from Oregon State University and studying acting at Carnegie Mellon University in Pittsburgh and American Conservatory Theatre in San Francisco, Jessup teamed with Ruth Hastings and Barry Lloyd in 1977 to form Ruth Hastings & Co. The trio played nearly every cabaret in San Francisco including Le Domino, Chez Jacques, Gordon’s, Fanny’s, Trinity Place and the Plush Room, culminating in a sold-out concert at the Geary Theatre, which was recorded live.
A highly successful run of Jacques Brel is Alive and Well and Living in Paris at Chez Jacques resulted in an invitation to perform the acclaimed musical revue in Brussels at the Belgian National Opera Company just after Brel’s death. The show was revived in a critically acclaimed run at the Stagedoor Theatre in San Francisco. After Belgium, the Company began a tour of the U.S. and Canada and played such Bay Area venues as the Concord Pavilion and the Venetian Room of the Fairmont Hotel.
On his own, Jessup, who was described by the San Francisco Examiner as “smooth, clever and quite wonderful,” has appeared in musicals and revues with Artstreet Theatre, Rohnert Park’s Pacific Alliance Theatre Company, Broadway by the Bay (San Mateo), California Conservatory Theatre, 42nd Street Moon, the Aurora Theatre Company and Marin’s Alter Theater Ensemble. Among his favorite roles are Mr. MacAfee in Bye Bye Birdie and a triple play of Jacob, Potiphar and Pharoah in Joseph and the Amazing Technicolor Dream Coat as well as Sen. Rawkins in Finian’s Rainbow, Gravvins in Cabaret Girl, C. Gordon Bennett in Miss Liberty, and Sir in The Roar of the Greasepaint the Smell of the Crowd…all with San Francisco’s 42nd Street Moon. In addition to performing in Mae West’s Sex with Aurora Theatre Company, he also played principal roles in the original plays Catherine’s Care and Thirst, both with Alter Theater Ensemble of Marin County .
Jessup has been interested in the life and music of Sir Noel Coward for many years, gradually adding more and more of The Master’s songs to his repertoire, eventually writing a script using Coward’s own words culled from his diaries and interviews. Jessup sold out the run of his one-man showcase Craig Jessup Sings Noël Coward at the Mark Hopkins Hotel, an evening that was described by the Contra Costa Times as “sophisticated…wonderfully bright and intelligent (not to mention very funny).”
In 2016, the San Francisco Chronicle wrote: "A veteran of cabaret stages for more than 25 years, Craig Jessup spans musical styles. He can be playful and twangy, or edgy and electric. His singing also has a narrative quality that betrays his musical theater background. Each lyric springs from a deep and distinct emotion; each bit of phrasing is carefully sculpted to communicate an idea with clarity and dynamism."