Jay Jason's interest in show business began when he would imitate the dialects of some of the residents from different countries who lived in boarding houses his parents owned.

[3] During World War Two, he entertained for the USO,[4] and during one show, he performed in front of hundreds of Hollywood and night club personalities including Red Skelton and Mickey Rooney.

This well known comedian, who has played many engagements in Toledo and has one of the largest night club followings…" [8] From the 1950s to the late 1990s, Jason was one of the most enduring and recognized performers at Catskill Mountains' resorts.

An entertainer for 60 years—impressionist, singer, even has a few dance steps in him…he’s played the Las Vegas hotels and Manhattan night clubs, appeared on The Ed Sullivan Show three times.”[10] Jason's humor had self-deprecating aspects, and all subjects were grist for his comedy routines.

He also impersonated celebrities such as Alfred Hitchcock, Jackie Mason, Jack Benny, Maurice Chevalier, Rudolph Valentino, Jimmy Stewart, the Hunchback of Notre-Dame, Arthur Godfrey, and Franklin Roosevelt,[11] and he also did voice-overs for cartoon characters.

[21] As an example, Martin Burden of the New York Post wrote: “Feud-in-the-making: Jack E. Leonard at the Blue Angel and Jay Jason at the Latin Quarter are telling the same quip: I always thought Chubby Checker was a fat taxicab.”[22] In addition, Earl Wilson of the Sarasota Herald-Tribune[23] wrote: “Today’s Best Laugh.

After moving throughout the Midwest for much of his early career, in the mid-1950s, Jay and Lynn settled in Teaneck, NJ, which allowed Jason easy access to the Catskills Mountains.

[44] Kramer is quoted as saying: “Through a friend of mine, I ended up getting a job as a chauffeur for a comedian named Jay Jayson,who was very popular in the Catskills.

This is illustrated by a newspaper story about his son's bar mitzvah: "The boy’s father is the current comedy star at the Latin Quarter in New York city.

Many show business personalities attended the service, including Jackie Mason, Phil Foster, Norman Dean, Lew Black, Davey Starr, Jack Kahane, Corbett Monica, Gene Baylos, Marilyn Maxwell, Tony Drake, Laura Lane, Tina Robin and Bea Kalmus.

"[48] At his daughter Diana's wedding, comedians who attended included: Reginald Stanbach, Lou Menchell, Allan Tresser, Dusty Brooks, Al Bernie and Murray Waxman.