Honestly, Dean was more talented, he was better looking, a better actor, and a better all-around guy, and his voice was as good as Frank’s (certainly from the late 50’s/early 60’s on).
Frank had about a 10-15 year jump on Dean, in the “fame” department. He was a HUGE “teen idol”, in the 30’s, before that was even a thing.
I have friend that knew both of them (she was in the music industry) and her opinion isn't very good in regards to Frank (or his daughter, Nancy) , she has nothing but good things to say about Dean.
To me, Dean's casual and comedic personality comes through his singing voice. Whereas Frank, while his voice is tremendous, is hollowly smooth. No heart in it when compared to Dean.
Mom was hooked on Perry Como and Tony Bennet but had nothing to do with the Rat Pack. To her, they were just a bunch of hoods.
You have to understand something; Las Vegas was Newport Kentucky, picked up and moved to the desert. When the mob went to the desert, they had a swinging scene just on the other side of the river from Cincinnati. There were several clubs over there. They ran gambling operations as well as entertainment. The vibe of Vegas was Newport with a bigger budget, and all the original personnel for Vegas came from Newport. Newport was also the training academy.
My Dad was in his prime at this point. Yeah, he knew a few crooners, but these were not the kind of guys he liked. Two guys I know he buddied with were Jackie Gleason and Cab Calloway. They were more fun to be around. Also, he hung with the WLW Radio crowd a lot, and was THE Guy to go to for a cheap apartment when you got to town, so all the other local TV guys were living in his buildings. Who he hung with the most were the Midwestern Hayride crowd. They had 3 bands that toured during the week and then had the big show that was on nationwide radio on Saturday night. A lot of the Hayride crowd found their way to Hee Haw. Kenny Price was at the top of that list.
The thing was, Dad and the rest of our family were kind of a competing interest to the people backing the Newport operation. Those boys wanted in North of the River, and the guys on the north side wanted to keep them out. Of particular interest to us was the building trades. Cincinnati was strictly non-union on residential construction. We stood in the way of those interests in Newport. In Cincinnati, The Mayor, the City Manager, the District Attorney and the Police Chief all had German last names, and they were all fond of partying at our family farm in Mount Healthy. For a while there, Dad's brother was besties with the Jake, thePolice Chief and used to double date with him and the wives. When Dad went along, they'd bring a young, beautiful chick along that eventually became the Chief's Sister-in-Law. You may remember her, Marge Schott. Marge had kind of thing for Dad, but he was not interested. Believe it or not, Marge Unnewehr used to be a looker. Yeesh!
A Sicilian friend of mine from Sandusky, Ohio asked me once, "Why is there no Mafia in Cincinnati?"
"La Cosa Nostra manga'd la lora nostra." -- mangled Italian for "Our Ting ate der Ting."
There is no reason to go into details, but when Dad would go to Newport in those days, he knew he was protected. As a result, he and the Italians did not party a whole lot together. That skinny kid from Hoboken and the big one from Steubenville gave him a wide berth. Frank was on his way down. Dean was on his way up. It's funny, because our family was rather beloved by the ethnic Italians on the north side of the river. To them, we were the ones who were giving them jobs and an entre into construction. I'm living in a house built by an Italian friend of my Dad. Dad went to him after he was too old to do a house on his own anymore. It's built right next to the Italian's home in the last subdivision he built.
This was the long way of saying "My family didn't think much of Dean or Frank."
Me? I grew up rather unaware of all the hoo-haw. All I knew was there was this big network of German home builders building on the north side of Cincinnati that treated me like family. I also knew that every TV personality in town knew my Dad. Doris Day was from Price Hill and Rosemary Clooney was from just up river at Augusta. The Midwestern Hayride was a TV show where Dad's tenants used be. Even the local kid show hosts knew who I was.
When the network TV shows used to come on, Dad would point to the screen and say something like, "I used to drink with him," or "I knew her brother." He was quiet about Frank and Dean.
My opinions of the two are unshaded by all this. What I can tell you is that Frank Sinatra wasn't worth spit to me as a singer before he lost his voice. He only attracted my attention after the comeback when there was a lot more character in his voice. When I first started to think about him as an actor was Von Ryan's Express. However, where I got to like him was the Tony Rome movies. It's weird, there's another connection. Those were shot in Miami, and I was going to Miami to visit my grandmother back then. Dad and the family would pick up and move operations down to Miami every year after Cincinnati got too cold to pour concrete. There was Mob down there, too-- just over on the other side of the island from our place. I felt like Tony Rome movies were being shot in Grandma's backyard.
As I get older, I have tended to prefer Frank. Frank was more of a stylist, and he was the first vocal recording artist to recognize the microphone as an instrument and use it as such. Frank's later stylizations are a closer to my own experience. I had to go through the comeback of having my voice damaged. This was years after giving up in Broadcasting, but it permanently changed my career in IT. I had to give up a lucrative network sales path.
Dean's stage persona is much more to my liking. He's got the better voice. He also has a quicker wit and incredible comic chops. He affected that slow witted drunk schtick, but behind it was a lightning-quick mind that used to leave Frank in the dust. If you watch the interactions between the two on Johnny Carson's show, Dean is clearly in the driver's seat.