It's difficult to pick only five, since Frank is one of my all-time favorites (no matter the genre of music--and I like a wide range of music). Of course, you could pick one of the many boxsets or compilations available, but you'll be cheating yourself. These albums were meant to be listened to side one and side two and in order (I know, heresy in this age of digital music and the option to buy single tracks--oh, by the way, we had that too when I was a kid (yeah, yeah, back in the 1970s), they were called 45s (tiny pieces of vinyl, in case you don't know)). Moving on...
I'm not sure these are the albums one would start with if they didn't know much about Frank, or tunes he sang beyond the obvious ones, but here goes:
This live album is a great place to begin. Why? The Quincy Jones arrangements coupled with the big band sound of the Count Basie Orchestra work perfectly with not only Sinatra's voice, but his showmanship and personality. I'd go to this album first because you also get a lot of banter and some monologues. The character of Frank's voice as he got older, say in his forties and fifties, is to me what sets him apart from other crooners, swooners, and so forth. The recording isn't perfect, his voice isn't perfect, but he's charming and funny and puts on a great show. "Luck Be A Lady" and "Angel Eyes" couldn't be more different, but both are outstanding.
For some reason, I tend to enjoy Frank's collections of torch songs the most. Only The Lonely is one of those, as if you couldn't tell by the title. The album cover painting won a Grammy Award. I'm not a fan of clowns--it seems most people aren't, even if this one is Pagliacci-like--but don't let the cover deter you from one of Frank's best albums. The first three tracks ("Only The Lonely", "Angel Eyes", and "What's New?" are wonderful but there's a longing in them, and the loneliness seeps from Frank's voice.
This is the first album Sinatra recorded in stereo. All of the tracks are great listens, but the standouts are "Where Are You?", "The Night We Called It A Day", and "I'm A Fool To Want You"--which you can hear the heartache, as if he's singing to Ava Gardner and how he can't help but love her. Another melancholy album full of torch songs, but I love it.
This is an upbeat album (you probably guessed as much), and Sinatra could have slipped a torch song in, but didn't (I think the closest he gets is "Saturday Night (Is the Loneliest Night of the Week). These are all upbeat tracks, and was Sinatra's most commercially successful album, staying on the charts for two and half years. This album also won 3 Grammys--Album of the Year, Best Vocal Performance-Male, and Best Arrangement. This is happy music and all the tunes are catchy.
Another uplifting Sinatra album, with loneliness, depression, failure in relationships, and so forth. Recurring motifs on many of Sinatra's covers are him looking depressed or lovelorn with a cigarette in hand, and a lamp post. This is the first in a string of Sinatra releases Capitol Records began calling concept albums. This is also one of the best albums of all-time. With this album we begin to hear the maturing of his voice and the character behind it (okay, so maybe cigarettes and alcohol had something to do with the change in his voice).
Okay, I'll toss out one more, and if you had to pick up a compilation or box set, I'd say go with this:
This 2 CD, 46 track, set is perfect for someone wanting a wide range of Frank's hits from his Capitol and Reprise years. These are the songs you've heard at some point in your life (I hope), but there are others on here you may not be familiar with. I have to admit, I'm not a fan of the more modern songs on here (or the ones where he's covering a pop song of the day, like "Bad, Bad Leroy Brown" or "You Are The Sunshine of My Life" or "Yesterday". But, one of the gems on here is a cool live version of "The Lady Is a Tramp" from a 1974 performance at Madison Square Garden. The mid-70s is probably the last time Frank sounded like the Frank I love of the 50s and 60s.
Now, I do love the Sinatra from the late 30's when he sang with Harry James and then into the 40's with Tommy Dorsey, that's great stuff. But do yourself a favor and give Sinatra a try, maybe on a day when you're blue, or maybe on a day where you feel like dancing or having a smile on your face. Sinatra is great to listen to while in traffic (the live albums in particular, or perhaps Come Dance With Me!.