In 1939, Red went to work for Minsky, the youngest burlesque comedian in the business. He billed himself as the "Only Burlesque Comedian With All His Own Teeth." In 1941, Jose Ferrer plucked Red out of burlesque for his first Broadway show, "The Admiral Had A Wife." The show was supposed to open on December 8, 1941, but it never did.
The show was a farce comedy about Pearl Harbor – great timing! 

In 1942, Red Buttons did "Vicki" on Broadway with Jose Ferrer and Uta Hagen. Also, in 1942, Red appeared in "Wine, Woman and Song" for Minsky. This was the last burlesque show in New York City since the La Guardia administration was determined to close it. Red was on stage when the place was raided. In 1943, Buttons, now in the Army Air Corp., was chosen for a role in Moss Hart's "Winged Victory." First he did the Broadway show, and then the motion picture for Darryl Zanuck with George Cukor directing. 

When "Winged Victory" disbanded, Red joined Mickey Rooney's outfit in France, and together with Mickey, entertained the troops all through the European Theater of Operations during World War II. Red had the honor to perform at the Potsdam Conference and was among the first troops to enter Berlin. After the service, Red did two more Broadway shows – George Abbott's "Barefoot Boy with Cheek" with Nancy Walker, and Michael Kidd's "Hold It."

From 1948 to 1952, Red Buttons played the Broadway movie houses with the big bands – the Paramount, the Loew's State, etc.; the cafe circuit – The Copa, Latin Quarter, etc.; television guest shots – The Milton Berle Texaco Hour, Cavalcade of Stars, and more. In 1952, came "The Red Buttons Show" on CBS. A smash! He won the Academy of Radio and Television Arts and Sciences Award (which later became the Emmy) as "Best Comedian of 1953." The series lasted three years, the last season on NBC.

In 1956, Red did "A Midsummer Night's Dream" with Basil Rathbone and Leopold Stokowski directing a new score written by Carl Orff. 1957 brought the film "Sayonara" with Marlon Brando, and Josh Logan directing. In 1958 Red won the Best Supporting Actor for "Sayonara" and the Golden Globe Award for Best Supporting Actor. 

A movie career followed with "Imitation General" with Glenn Ford, "The Big Circus," "Hatari!" with Howard Hawks and John Wayne, Darryl Zanuck's "The Longest Day," a cameo in Billy Wilder's "One, Two, Three", "A Ticklish Affair," "Your Cheating Heart," "Gay Puree" with Judy Garland, "Five Weeks In a Balloon," "Up From the Beach," "Harlow" (for which he was nominated for a Golden Globe Award for Best Supporting Actor), "Stagecoach" (the remake), "They Shoot Horses Don't They?" (for which he received another Golden Globe Award Nomination for Best Supporting Actor) with Jane Fonda, "The Poseidon Adventure," "Gable and Lombard," "Movie, Movie" with George C. Scott, "Viva Knievel," "When Time Ran Out," "Off Your Rocker," "Reunion at Fairborough" with Robert Mitchum and Deborah Kerr, "The Ambulance" with Eric Roberts and James Earl Jones, and "18 Again" with George Burns.

In 1966, Red Buttons did the ABC television series, "The Double Life of Henry Phyfe." He guested on every major television show – Ed Sullivan, Andy Williams, Dinah Shore, Perry Como, Redd Foxx, Eddie Fisher, Johnny Carson, Merv Griffin, Mike Douglas, Bill Cosby Show, and Dean Martin Roasts (where he did his famous "Never Got a Dinner" routine). Dramatic shows included "Playhouse 90," "U.S. Steel," "Studio One," "General Electric," "Knotts Landing," and the Emmy Award winning series "E.R."

Specials included "Louis Armstrong, Chicago Style" with Ben Vereen, "Telethon Power," "Leave 'Em Laughing" with Mickey Rooney, "The Users," and "George Burns 95th Birthday Special." Red was a frequent guest star in the gambling palaces of Las Vegas, Lake Tahoe, Reno and Atlantic City. He wrote and recorded a children's album of poems on the Golden Record label entitled "Poems for My Daughter and Other Little People, Love Daddy."

Red Buttons has a star on Hollywood and Vine – full circle for a ghetto kid who started by entertaining on street corners. Red Buttons was honored by The City of Hope "Spirit of Life" Award, the Eddie Cantor Foundation's "Suzie" Award, the Friar's Club "Lifetime Achievement" Award, and the Junior Achievement Award for his charitable
contributions to all causes.