Let’s see, my band and I would open with “Rock and Roll, Hoochie Koo” followed by “One of These Days”, and finish with “Space Truckin’”. That medley should do a number on the sock hoppers.
Lady Cab Driver - Prince
Smells Like Teen Spirit - Nirvana
and just because I’m a jerk, and to prepare them for their future hell, I’d get a girl to do
I Kissed a Girl - Katy Perry
I THINK the kids might get into it, the chaperones… well, “somebody get a rope”
Harder, Better, Faster, Stronger - Daft Punk (you could wear the Darth Vader from Vulcan costume)
Californication - Red Hot Chili Peppers
American Pie - Don McLean. You’d be a 1950s musical Nostradamus.
No, have an early Beatles, an early Stones, and an early Who! Start with She Loves you, then shake them up with Satisfaction, and finally blow their minds with My Generation.
Yeah, I thought of that, but then I heard Alice in my head saying, “Cadaver eyes upon me see…nothing,” and I was forced to obey.
I’d open with Smoke on the Water, sail into My Generation, and close with a perfect Hendrix-esque Star Spangled Banner to appease the faulty.
Elton John’s “The Bitch Is Back” might also get a similar reaction. It would really shake them up, that’s for sure. 
“Tomorrow Never Knows”, The Beatles
“Kiss”, Prince
“Ether”, Gang Of Four
Just to trip them out.
- Red House (Jimi Hendrix)
- Going Home (From the movie Woodstock - Ten Years After)
- Mexican Rap (from the movie Double Take - I think it’s Delinquent Habits)
The crowd would either sht or go blind. The chaperones would faint. Anyone who spoke Spanish (not likely in that crowd) would sht, go blind, AND faint. And I’d be the rock star of the century, bwah-ha-ha!!! (If I got out alive, that is…)
Assuming I get to perform exactly as the real artist, I’ve always wanted to be David Bowie.
Changes
Golden Years
Wild is the Wind
“Wanna Be Starting Something” by Michael Jackson
“The Real Slim Shady” by Eminem
“TiK ToK” or maybe “Fuck Him He’s a DJ” by Kesha (whichever one I don’t pick will be the encore if nobody shoots me first. Any references to men would be changed to women so as not to do the gender bending thing.)
Michael Jackson’s song may sound out of place, but nothing too offensive for the chaperones, and the kids would probably enjoy it. The last two would probably result in a public whipping, and nobody would know why the hell I was speaking instead of singing.
Billy Joel’s We Didn’t Start The Fire would blow their fucking minds later.
Taking this question semi-seriously, this is the best answer so far.
You’d have to start with nothing later than early Beatles to bridge the gap, and I can’t think of any better ‘bridge-gapping’ band than them. But you couldn’t go too much farther ahead. You could only play songs that ‘got-up-and-go’ pretty quickly, Pink Floyd et al. wouldn’t have a chance. Anything from the early 80s would confuse them, and most any kind of Rock 'n Roll from the late 80s to the present would just sound like noise to them.
I’m with you on #1 and #2, but how about Born This Way for #3? It’s catchy, it’s upbeat, it’s oh my lord what is that singer saying?
Speaking of born, how 'bout Born To Be Wild?
Is my time machine idling outside the door so I can make a quick escape? Yes? Then…
I’d get them comfortable with Benny Goodman’s* Sing, Sing Sing*, then mess with their feet with Brubeck/Desmond’s Take Five, and then put on The Rodeo Song by Garry Lee & Showdown and run for the door…
It’s a prom, right? So how about Meatloaf’s “Paradise By The Dashboard Light”?
Maybe preceded by The Cars’ hit “You’re All I’ve Got Tonight”, and to wind down those raging hormones, “Relax” by Frankie Goes To Hollywood. 
Slow ballad: “Who’s Loving You” by the Jackson 5, and current hit “Just The Way You Are” by Bruno Mars.
Baba O’Riley, by The Who
Tom Sawyer, by Rush
And then something just for fun. Pick one:
Bohemian Rhapsody, by Queen
Mmmbop, by Hansen
It’s Raining Men, by The Weather Girls
The Safety Dance, by Men Without Hats
I Wanna Be Sedated, by The Ramones
Walk The Dinosaur, by Was (Not Was)
Mr. Blue Sky, by ELO
This is me, so you know I’d go all viking metal on their 1950’s asses. I’d start with something by Enslaved, say, ‘Ethica Odini’. Then I’d move into Amon Amarth’s ‘Twilight of the Thunder God.’ And I’ve gotta give some love to Tyr. I’m thinking ‘Hold the Heathen Hammer High,’ but really, anything by a band of Faroese pagans would do.
As to the reactions, I have no idea what would actually happen. Hell, chaperones in 2011 America probably wouldn’t know what to do. In 1955… I have no idea, but the aftermath would fun as hell to watch.
“I Don’t Like Mondays” by the Boomtown Rats. Everyone would be dancing to the catchy tune until the chaperons catch on to the lyrics.
“Willie the Pimp” by Frank Zappa
“You’re Breaking My Heart” by Nilsson.