Title says it all. Assume, since this is a fantasy and all, that your backing band (and you too!) has the chops to play whatever it is from 1956-now that you select.
What do you play? How would the crowd react? Hell, how would the chaperones react?
The Trashmen’s Surfin’ Bird
Tom Lehrer’s So Long Mom, I’m Off to Drop the Bomb
Laurie Anderson’s O Superman
I would expect to be pelted with drinking glasses and toilet paper, and maybe given a swirly by a deputization of football players.
ha ha ha ha ha ha ha ha
I don’t think you could do better than '80s pop rock if you’re looking for stuff that’ll appeal to a group of '50s teenagers. '60s and '70s were too counterculture and would be way out of their experience. There’s probably stuff from the '90s on that would be good, since stuff’s gotten so varied.
For myself, I’d kind of like to see the reactions to:
Guns 'N Roses - Sweet Child O’ Mine
Big Bad Voodoo Daddy - Go Daddy-O, or any other '90s swing music
Anything from Michael Jackson, but probably Billie Jean or Thriller
Well, if you don’t play Johnny B Goode, then Chuck Barry wouldn’t be able to steal it and pass it off as his own, and the song wouldn’t exist. And since I like that song, I’d sort of have to play it so that I could still enjoy it in the future.
Springsteen’s ‘Born in the USA’
REM’s “End of the World”
Tom Petty “Refugee”
These would be kinda reocgnizable to 50s folk as rock, but the subject matter might have them scratching their heads. which is fine.
This is a surprizingly easy question. I’ve known the answer since before that movie came out.
Dazed and Confused
Faeries Wear Boots
Shine On You Crazy Diamond
The audience’s reaction? They’ll hail me as a freakin’ genius.
I’ve actually know this since I was, oh, 16.
I’d definitely play something from “Sergeant Pepper’s Lonely Heats Club Band,” perhaps “A Day In the Life.” Something by Jimi Hendrix, either “Purple Haze” or his cover of “All Along the Watchtower.” And maybe something by Led Zeppelin. “The Immigrant Song,” or possibly “Kashmir.” Or maybe even “Moby Dick.”
Maybe for an encore I’d do “My Generation.”
They’d probably be all scratching their heads like when Marty went into the guitar improv at the end of “Johnny B. Goode.” But hey, give them about ten more years and they’ll be groovin’ on it.
I’d do early Beatles, like “I Wanna Hold Your Hand” and “She Loves You Yeah, Yeah, Yeah,” etc. Just a tad into the future, so the audience should find it acceptable, but still groundbreaking.
Oh, this is easy:
Whole Lotta Love, Led Zepplin
Rock Lobster, The B52s
I Love the Dead, Alice Cooper
I would expect stunned silence through the first song and then, after they finished dancing against their will to my second selection, a host of enraged citizens chasing me around with pitchforks and torches while I finish the set.
Freeeeebiiiirrd!
Something by Hendrix - Are you Experienced?, perhaps.
And I’d still play Johnny B. Goode, because it’s an awesome song.
That might get you that result, but if you want to guarantee it, replace your third number with Dead Babies.
Some awesome instrumentals, maybe.
Frankenstein - Edgar Winter Group
Hocus Pocus - Focus
YYZ - Rush
(Okay, maybe those need more than just a guitar…)
“White Lines” by Grandmaster Flash
Nothing else, I’d just play it 3 times.
Seek and Destroy - Metallica
Paranoid - Black Sabbath
We will rock you - Queen
I’m going with songs that I think the audience might like and relate to but that would also seem new and different. It would be tempting to try and shock and awe them with something more extreme.
My picks:
*Rebel, Rebel *by Bowie
That’s What I Like About You by The Romantics
Wicked Game by Chris Issac
Someone posed a somewhat similar question to me years ago, except it was along the lines of: “If an alien came down to earth and wanted to know what rock and roll music was, and you were only allowed one song to play for him to define the genre, what song would it be?”. I thought about this for a while and ultimately decided on Gloria by Them. Three chords, a hard driving beat, and screeching about sex - it perfectly sums up rock.
I guess for this scenario, my other two songs would be… Anarchy In The UK by the Sex Pistols and, well, Johnny B. Goode. I don’t think they’d particularly take to Anarchy, but that’s kind of the point, isn’t it?
Open with: Sympathy for the devil by the Stones
Slow things down with: Stripped down version of Home Sweet Home by Motley Crue
Close with: Born to Run by Springsteen which will (in my mind) just blow the roof off the sucker…
This is one I’ve spent probably more time than is healthy thinking about before. 
If I had a time machine, there are hundreds of songs I’d want to steal and play for earlier audiences.
I wouldn’t want to be Marty McFly; I’d rather be myself, with a voice worth listening to, of course. And with a backing band I’d had a chance to rehearse with. Most of those songs I’d like to play were originally by male artists, and end up displaying interesting twists on the power relationship between the sexes even if the lyrics are altered to keep them heterosexual songs.
But, limited to just three, I think I’d just stick to Grrl songs:
“Dreams”, Cranberries
“Just a Girl”, No Doubt
“Bitch”, Meredith Brooks. Strickland would be charging the stage to shut us down the instant we hit the first refrain, so perhaps change that word to “witch” in the lyrics.
If we didn’t have to worry about Strickland et al shutting us down, I wouldn’t change “Bitch” and I’d replace the first two songs with these to see the reactions:
“Manic Monday”, Bangles (woman works 9-5 to support her unemployed boytoy)
“I Kissed a Girl”, Jill Sobule (not the completely different song by Katy Perry)
*** Ponder
Paranoid Android by Radiohead,
I Confess by English Beat,
and, of course, Fuck You by Cee Lo Green.
I’d play “Summertime Blues”, “Peggy Sue” and “Whole Lotta Shakin’ Goin’ On”.
The audience would go nuts, a talent scout in the audience would sign me up and I’d go on to be bigger than Elvis (assuming of course that I could keep churning out hits a couple of years ahead of their time).