Frank made it big singing for the swing bands in the late 1930's early 40's (first with Harry James and later Tommy Dorsey). Later during World War II, The Voice struck out on his own and was probably responsible as much as anyone for the rise of the singer to the detriment of the instrumentalist in popular music.
When it looked like his recording career was slowing down, Frank began starring in Hollywood films and most weren't all that bad. But what was really a surprise was that Frank was far better playing dramatic non-singing roles, one of which, his supporting role in From Here to Eternity, actually garnered him an Oscar. He ended up as the top paid entertainer of his time and was still putting out #1 songs on the Top Forty when the bobby soxers who had sent him to the top were long gone. If you can find a record store still open somewhere, you'll probably find one of the largest bins holds the CD's of Old Blue Eyes.
But for all his appearances - on film, television, or live - one was not what you'd expect from a hip sophisticate like Frank Sinatra. And regardless of what you hear of Frank's more seamier connections and cantankerous nature, you can't but help like him for it.
In the 1960's, Frank, along with Sammy Davis, Jr., Dean Martin, and the others of the "Rat Pack" appeared on the kid's show hosted by Soupy Sales. Soupy's program was somewhat on multiple levels. Older kids and even adults liked the show, not the least reason being that he had non-kid celebrities as guest stars long before it became standard fare on Sesame Street.
But for those who remember Soupy's show, you can guess the final outcome. Yes, by the time the skit was over, The Chairman of the Board ended up with a pie in his face.