Like Marley with straight reggae (not reggae-influenced rock), he's a genre dead-end for vocal jazz that will appeal to erstwhile prog/classic rock/metal/hard rock/grunge dorks like me 'cuz for most of his career he specifically set out to record concept albums and not just haphazard singles/tossed off covers chosen by record company executives to pad singles collections. Great deep voice too. Yeah, nearly all of his songs were covers of first half of 20th century Broadway songs that most people wouldn't otherwise seek out on their own, but he made the definitive version of most of them as far as I'm concerned. Not like I'm gonna try out Bing Crosby or Tony Bennett catalogue as a comparison.
Well, I did bundle Bobby Darin and his daughter Nancy into my Sinatra phase/exploration of his discography. Made a 21-song hits collection for Darin and 14-song one for Nancy cuz' I dig the cowboy psychedelia of Some Velvet Morning. Have dug the Mack the Knife song for a while as an early example of art-rock though it's blasphemy for suggesting that, but just like Michael Jordan had many short-lived pretenders to his throne in his hey-day, most of them fell by wayside, though for a hot sec in '59-'60 Darin was really legit competing with Frank to the point Frank had to knock him down a peg. I mean I listen to Testament a lot because I have an itch for 80s Metallica that isn't actually played out 80s Metallica, i.e. relationship Darin and I guess Tony Bennett has to Sinatra, though I'll probably never have a Tony Bennett phase even though he did albums with Gaga.
Anyways, here's how I organized Frank's discography:
36 songs from his '39-'42 stint as merely the 2nd banana singer to the bandleader
46 songs from his '43-'52 Columbia years when he went solo though that stint kinda petered out at end
Every single one of his Capitol albums from '53-'62 minus the Christmas album
The Reprise Years when he went out on his own starting in '61 was fun to organize in the same way Prince after '88 discography fun to organize 'cuz there's a lot of gems with some schlock and experiments you never need to hear again. He also had a tendency to re-record songs he only recorded like 5 years earlier on his prime Capitol stint that doesn't sound drastically different unlike rerecording his 40s songs in the 50s did. Albums I discarded and salvaged the notable songs for compilations from Reprise are: I Remember Tommy, Sings Great Songs From Great Britain, the 2 albums with Basie cuz' there's a lot of recent repeats on them and they aren't mostly better than the 50s versions though new songs are great, Sinatra's Sinatra, the album with the really long title of then recent movie songs, the album of patriotic songs, 2 Christmas albums, My Kind of Broadway, the bossa nova album with Jobim that's kinda meh especially when you have a huge ass discography plus I don't like making separate iPod headings unless I absolutely have to, the album with Duke Ellington, A Man Alone, Sinatra and Company, Some Nice Things I've Missed, and the last solo studio album he ever recorded LA is My Lady in 1984 with Quincy Jones that's as bad of a generic synth trying to keep up with the Jackson's imitation as it sounds. Everything else on Reprise interesting and worth keeping.
I'm also never gonna listen to those 2 Duets albums he made in his 80s cuz' those songs are repeats.
Oh yes, he did actually record a Frank Zappa-esque prog suite on the last disc of his 1980 Trilogy album and it's neat.