I just recently rediscovered Sinatra. He had a truly beautiful voice - especially when he was younger. From what I remember about him and what I have read about him he was somewhat less than a model citizen or even a decent man. But he was a genius when he sang.
Stephen Colbert (sans glasses) is built a lot like Sinatra. Don’t know if he can sing or not.
Here's a story. A close friend's family was in the livery business in Chicago. They were contracted for a theater opening back in the 60's to which Sinatra was present. My friend happened to be slated the driver of comedian Jack E. Leonard that stormy night. He picked up Leonard at the hotel just before Sinatra's driver arrived. All the way to the theater Leonard acted the big a$$ and by the time they arrived, my friend had had it with him.
Instead of driving up to the canopy over the red carpet, my friend pulled up across the street and made Leonard walk across in the rain. Just before pulling away, someone knocked at his driver window; it was Sinatra's driver. The driver handed my friend a $100 bill, saying it was with Mr. Sinatra's compliments. "He can't stand the SOB either".
Some years ago this story was supported by a TV special I watched about Sinatra. In it, friends told of how Sinatra would carry $100 bills with him, handing them to body guards or friends to see that someone who did him a good turn or provide service beyond that expected would receive this extra tip.
Sinatra may have had anger management issues, but he had a big heart. And he went out of his way to help others he found in need.
I've been a Sinatra fan since my early teens (I'm 65). There will never, ever, be another singer, IMHO, who reaches one's soul as Sinatra did with his ability to interpret music.
Yes he can, a very good voice, he has done musical theater. I don't know that he could imitate Frank, but then, I would never have believed the guy who starred in the Disney film, The Man from Snowy River could either, but in the CBS miniseries several years ago, (Tina okaying everything), Australian actor Tom Burlinson was the singing voice for the early Sinatra numbers. It was an amazing feat!