I want to get into Frank Sinatra. What album should I start with?

Songs For Swingin’ Lovers! Is my personal favorite, I feel like you outta like it.

I’d suggest starting with the Ultimate Sinatra compilation. That will give you a comprehensive sense of his eras and you can delve deeper from there.

In The Wee Small Hours if you want sad ballads. Sinatra's Swingin' Session if you want to hear him at his greatest. Songs for Young Lovers if you want a smaller, almost cocktail jazz sound. Watertown if you want a later, rock-influenced concept album. 

I also have a playlist with (nearly) all his songs chronologically if you are interested. His early stuff is very different. He began in 1939 when jazz crooning was old news and soft, semi-operatic ballads were getting big, so much of the early stuff is gonna be slower and quieter than his later Swing records. 

Sinatra is my absolute favorite singer. I'm in love with his voice, the way he phrases things, and perhaps most importantly the bands that played with him and the wonderful arrangements they played. If you like Sinatra, look into Nelson Riddle's instrumental albums as well. 

https://youtube.com/playlist?list=PLu63EmDl_V2M9yhiSCeRkvhYtwoMYgRsC&si=uFmbg4-MW6qiESEh

Upbeat songs - Songs for Swingin’ Lovers! Ballads - Frank Sinatra Sings for Only the Lonely

“Sinatra And Swingin Brass” is imo his best starter album, he’s in solid voice and has great arrangements, songs, lyrics, some big hits and lesser known cuts from a great period for him and his career. “Serenade In Blue”, “Tangerine”, and “I Love You” are my personal favorites

I got into him by buying his latest greatest hits album; Ultimate Sinatra. You can currently pick it up at Target.

From there I started listening to his live albums. Live at the Sands is great. The Main Event Live is also great.

Then I started picking up his studio albums. September of My Years, Come Fly with Me, In the Wee Small Hours, Songs for Swiggin’ Lovers, and Come Dance with me are all great albums.

Frank recorded with three record labels during his career: Columbia, Capitol, and Reprise (which he founded). As mentioned by others, the Ultimate Sinatra compilation compiles songs from all 3 labels and is a fantastic introduction. I'd recommend listening to the Centennial Collection version because it has a lot more songs. From there, you can find out which songs you like more and then check out specific albums based on the label those songs are on.

Columbia is 1940s Sinatra, when he was still young and developing what would become "the voice." Capitol is 1950s/early 60s and is typically regarded as Frank's best work. This is when he essentially created the "concept album" which resulted in some of the best music ever made. Finally, the Reprise era, which is everything from the 1960s onwards (except for his final two Duets albums that were on Capitol), is probably his most "diverse" era. You still have a lot of jazzy, swingy standards that he was known for, but you also get some more experimentation with more "pop" sounds of the time. The album you listened to comes from the Reprise era.

But yeah, Ultimate Sinatra is easily the best compilation you can start with, then go from there. Have fun! :)

Classic Sinatra 1953-1960 is my favorite compilation

A great starter is the Capitol compilation "The Capitol Years" from 1990

I started with his songs with Tommy Dorsey! Essential Frank Sinatra with Tommy Dorsey

“Nothing but the Best” was the compilation that got me into Frank and does a great job capturing his range. You might find yourself drawn to different eras.

Strangers in the night!!!!!!

Sinatra at the Sands.

i am obsessedddd with frank’s early recordings, especially with tommy dorsey, so i suggest this compilation album!! and this playlist!!

When I was around 18 a guy in the apartment next to me was playing In the Wee Small Hours. He said to pick it up in case my girlfriend breaks up with me. Evidently he could forsee the future. I soon discovered sad songs make me happy.

My introduction was his “Duets” album.

The best album to start with is the only the lonely if you want to hear greats lyrics by Nelson Riddle that's the album to start this was a period of Sinatra life of headache which Ava harder was leaving him his music was selling tragic of Marilyn and Sammy Cahn. This album is a period of the best of frank Sinatra. People say classics or weed small hour albums are good too but this is hands down is much better. I'm a Sinatra expert. I studied his music for 20 years I'm only 35 and I'll tell you hands down the best singer of the century.

Start with The Future on the Sinatra Trilogy. 

Do better. Only the Lonely. If you want a faster vibe, Swingin Session! Or look for songs like Live til I Die. Don’t settle for Something Stupid, the name speaks for itself.