Chet Baker - Chet Baker Sings
The prince of cool, singing and playing. His sound is tender and intimate, but still laid-back enough for you to savour it slowly. A unique aesthetic that many imitated, but nobody achieved. "My Funny Valentine" and "The Thrill is Gone" are an excellent introduction to Baker's world. As a trumpet player, helped me through some tough times.
Curtis Fuller - Blues-ette
Legendary NY based trombonist who played on our subreddit's second favourite jazz tune aka Blue Train (the first being So What from Kind of Blue, judging from posts and comments). It's one of my go-to albums to listen to while walking at night in the winter, but it feels at home on your turntable too. Light up a cigarette and pour out a glass of whisky, and you got yourself a 50s jazz club.
The Dave Brubeck Quartet - Jazz Impressions of Japan
Some personal bias comes into this; it definitely wouldn't make an appearance on most people's top 50, even. If you ever make a trip to Japan, however, I recommend giving it a shot. "Fujiyama" and "Koto Song" express the Japanese harmony of traditional and modern. Listen to them while walking on a busy street, or on the train, you'll understand instinctively.
Duke Ellington - Masterpieces by Ellington
Ellington at his best, guiding his orchestra through a sensual, slow pace for "Mood Indigo", which features an unknown Yvonne Lanauze on vocals and the infamous Cat on trumpet. Another interesting thing to note is that this album was one of the first Long Playing records. That's right, one of the first jazz 12-inches. Duke, no longer confined to three and a half minute tunes, gave the tunes adequate time to expand and seep into your brain. Only two tracks a side, but more than enough jazz for a rainy afternoon. I suggest listening to "Mood Indigo" and "Sophisticated Lady" for starters.
If anyone needs a recommendation on what to listen to, feel free to PM me, I'm here all week.