What would be on it?
To recap, Captain America (aka Steve Rogers) "died" in 1945 saving New York city from a Nazi attack. He actually survived, but he was trapped in ice for almost seventy years. The current films show him waking up in 2013, in a future he could never have anticipated.
He's had some catching up to do.
In 'Winter Soldier', we saw that Steve was keeping track of various events and pop culture phenomenons that he missed.
(Fanart by kelslk)
He's probably glad he missed disco.
For the most part, Steve has adjusted to the modern world. so it stands to reason he'd have an iPod right now. He was born in 1918, but mentally and physically he looks more like a Millennial. It would be weird if he DIDN'T have headphones in during his downtime. Here's what I think he'd be listening to...
Ramble On- Led Zeppelin
Aside from being an absolutely beautiful song, I think there are a few reasons why Steve would be listening to this. The lyrics are really evocative, and I think they reflect the strange new journey he's found himself on.
Leaves are falling all around, It's time I was on my way. Thanks to you, I'm much obliged for such a pleasant stay. But now it's time for me to go. The autumn moon lights my way. For now I smell the rain, and with it pain, and it's headed my way. Sometimes I grow so tired, but I know I've got one thing I got to do...
Maybe I'm just projecting, but isn't that part of the fun of being a fan?
Finally, I have on really nerdy headcanon that makes this song fit perfectly. The Hobbit was published in 1937, so there's a chance that Steve might have read it. However, the Lord of the Rings trilogy wasn't completed until after the war was over. Steve wouldn't have known how it ended! I imagine that as soon as he adjusted to 2013, he'd want to find out how his favorite books turned out. The references to the books in the song would probably feel like a piece of the past that the future saved for him.
Working Class Hero- John Lennon
Most people don't realize this, but Captain America wasn't written to be a conservative symbol. Before he received the serum that gave him his strength and invulnerability, Steve Rogers was sickly and poor. He was raised by an immigrant single mother. In the 30s and 40s, Steve Rogers would have been the target of eugenicists, xenophobes, and classists. It was only later that he become the hero we recognize today, and his image was co-opted to be a patriotic symbol of traditional masculinity.
Captain America was the original working-class hero.
And he's probably have a few choice words to say to our modern-day bullies. Can't you imagine him listening to this, getting amped up before a rally or protest?
Jazz Police- The Big Phat Band
That all being said, I think Steve would really miss big band music. In 'Winter Soldier', Harry James and Kitty Kallen's 'It's been a long long time' was playing on his turntable. An alternate opening revealed that Steve still feels like he abandoned the people that needed him in the 40s (the scene is the second video on this block).
Steve Rogers is a man out of time.
I think he'd do his best to catch up on the decades he missed, but I also think he's seek out the genres of music that he was used to. There aren't many big band players anymore, but I'm sure Steve would find them. It might be comforting to discover others with similar interests.
New York- Angel Haze & Brooklyn We Go Hard- Jay-Z feat. Santigold
He'd want to catch up, too. Hip-hop developed while Steve was in the Arctic, but once he got used to the rhythm and language of the genre, I suspect he'd really appreciate it. Especially the streak of Brooklyn pride that a lot of artists have. In 'The First Avenger' Steve stared up defiantly at the Red Skull, stating: "I'm just a kid from Brooklyn." He doesn't think of himself as a hero.
I'm a Brooklyn boy I may take some gettin use to Chain snatchin, ain't have it, gotta get it Same shitted, from Brownsville to Bainbrididge Fatherless child, mama put double shifts
Those lyrics would definitely resonate with Steve. The landscape of Brooklyn has definitely changed, but some of the same spirit is still there. I think Steve would find comfort in that.
(Fanart by ferowind).
Obviously this is all speculation.
The films and comics are great. They hint at the difficulty of adjusting to the 21st century. But they don't have the time to explore that conflict in-depth. I guess that's what fic is for?