If I got to choose which decade to live in, I'd pick the 50's (minus the racism and nuclear missile scares). However, the closest I can get to living out my Old Hollywood glamour fantasy without a time machine is listening to 50's music. These are my opinion (in no particular order, of course). Please don't sue.
1. "Everyday" By Buddy Holly
"Only the good die young" certainly applies here. Though he passed away in a plane crash at the tender age of 23, he left behind an incomparable legacy. I personally think that, of his many hit songs, this is the best.
2. "Mr. Sandman" by The Chordettes
I don't know why I love this kind of female barbershop quartet sound, but I do, and I want more of it.
3. "A Teenager In Love" By Dion & The Belmonts
This song is a time capsule, which is to say that it reminds me of a place and time that I've never experienced. It's the closest you can get to being a high schooler in Grease.
4. "Who Put The Bomp (In The Bomp Bomp Bomp)" by Frankie Lymon & The Teenagers (Original by Barry Mann)
When I first heard this song I thought it was a joke, but I've come to love it. It's cute, catchy and a little weird: the perfect combination.
5. "Dream Lover" by Bobby Darin
I have no idea why all of these are love songs, but I think this is the one that truly transcends time the most. It's applicable and adorable even today.