I think there should be more 1950s era "rock music."
Myself... I don't think they'd be playing 1950's music in 2077 onward (except by styled "chance", for some dramatic in-game cutscene).
I look at the series prior to #3 and can only assume that they had their 60s, 70s, and 80s era culture ~always influenced by their 50's aesthetic... but only as an approach to design.
How would a Ipod be in their future (as opposed to "They can't have Ipods! They didn't exist in the 50's!").
My (private) assumption is that 'Lawrence Welk' and 'Ed Sullivan' didn't get cancelled, and Woodstock got raided before it started to rain; but that groups like Cameo and Toto would have had their altered equivalents; perhaps keeping to 50's beat patterns, and never losing aspects of 'Swing' as a crowd-pleaser. IMO the 50's aspect of Fallout (while real and entrenched in the core setting), has been a bit misconstrued in later years, by uninvolved developer teams... I really wish one of the original crew would go on record proving me wrong or somewhat right.
They invented the setting from scratch after all... In terms of origin, their opinion is the rule, no?; (and I don't mean Chris & Josh).
**As for an 80's choice... Nothing would beat http://www.youtube.com/watch?v=N1tTN-b5KHg while using a super sledge; or (70's) playing http://www.youtube.com/watch?v=x1mV_5-bRPo in some mad science lab fighting FEV reanimated zombies (or "http://www.youtube.com/watch?v=YXyFy7ixr10" while fighting robotic snipers in the same lab).
Or (lastly... and this ones' really bad); playing "I'll stop the world, and melt [with] you!"