You may not know this, but the 90s weren't the only decade to reintroduce older music styles.
https://en.wikipedia.org/wiki/Ragtime#Ragtime_revivals
https://en.wikipedia.org/wiki/Swing_music#1950s-60s:_swingin.27_pop
https://en.wikipedia.org/wiki/1950s_in_jazz
I for one would be receptive to new music in old styles. The fallout universe timeline seems incomplete without a music history past the 1950s.
Why not push the limit with some Post Modern Jukebox to fill out a playlist in addition to retro 90s fare? NOTE: I WOULD PAY FOR THIS IN A MOD/DLC. [...also as well as a good VCPR type talk radio station]
Radioactive [Jazz]
https://www.youtube.com/watch?v=RCWBxxEJiGc
Living On A Prayer [Jazz/Blues]
https://www.youtube.com/watch?v=RMeN0CFNWmk
7 Nation Army [Blues]
https://www.youtube.com/watch?v=sB6HY8r983c
We Can't Stop [Doo Wop]
https://www.youtube.com/watch?v=pXYWDtXbBB0
Sweet Child o' Mine [Blues]
https://www.youtube.com/watch?v=kJ3BAF_15yQ
Thrift Shop [Ragtime]
https://www.youtube.com/watch?v=4Cnm0tdkJEU
I Believe In A Thing Called Love [Vintage New Orleans-Style]
https://www.youtube.com/watch?v=FQwpQM2JDXg
Call Me Maybe [Ragtime]
https://www.youtube.com/watch?v=5meWI3iX1sE
Someday ["Casablanca Style"]
https://www.youtube.com/watch?v=Mwuq8GI8LME
Hey There Delilah [Vintage 1918 "World's Fair" Style]
https://www.youtube.com/watch?v=0IjiM7KjOzs
...and a cover of Queen's "Don't Stop Me Now"
https://www.youtube.com/watch?v=FxLR6cP1_Q8