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Good Medley/Mashup Suggestions:

We used to do a killer medley from Zep's first album.

Dazed and Confused
Good Times Bad Times
Communication Breakdown
How Many More Times
Then back to Dazed and Confused

It was pretty killer and everyone used to eat it up. And it used to kill almost half a set.
 
Sweet Home Alabama--->>All Summer Long (Kid Rock)--->> Werewolves of London--> back to Sweet Home
They are all pretty much the same song

Yes, I have done this. As "eye rolling" as it may be, it always goes over well.

Another one I've done along the same lines is Mustang Sally into Chain Of Fools.

Just before our breakup we were working on a mashup of Dierks Bentley's "Am I The Only One" and Dr. Hook's "Cover Of The Rolling Stone".
 
-"Compass" (Lady Antebellum) & "Some Nights" (fun)
-"Timber" (Ke$ha and Pitbull) & "Swingtown" (Steve Miller)
-"War Pigs" (Black Sabbath) & "Back In Black" (AC/DC)
-"Sharp Dressed Man" (ZZ Top) & "Gemini Dream" (Moody Blues)
-"Shake Your Hips" (Rolling Stones) & "La Grange" (ZZ Top)
-"Babe I'm Gonna Leave You" (Led Zeppelin) & "25 Or 6 To 4" (Chicago)
 
at the school I teach at, we have a "teachers" rock band that closes the annual Battle of the Bands that we do. This year, our mash up medely was the first half of War Pigs, into The Ocean, into Back In Black into the end of War Pigs. I didn't think that the kids would even recognize some of those songs, but it went over pretty well. We also do some more recent stuff as well.