In recent decades, there's been a proliferation of the "jukebox" musical, a musical show that takes a collecton of songs of a group or of a period, and tries to wrap a story around them. Unfortunately, what might seem like a simple way of creating a musical is not at all simple.
Most musicals fail because of a weak or non-existent book - the play/story component of the show (dialogue and stage directions). In other words, creating a viable story for a group of songs that were never intended to be part of a show is a real challenge. (See pages 244 and 311-312 in Playwriting for Dummies.) I speak from experience (www.thedevilsmusic.biz).
And then there's the 800-pound gorilla in the room: the unavoidable necessity to get (and pay for) the rights to use any music created after 1923. Never assume music rights are readily available and easy to acquire. Check it out before getting to deep into your project. And never ever stage a show using someone else's music without written permission. You will be sued, "you" meaning you, the show's creator.
The bottom line is, it's not enough to have a collection of "can't-miss" songs. Audiences go to musicals for the music, yes, but also for an engaging and entertaining story. Resist the temptation to skimp on the latter. For every Jersey Boys and Mamma Mia, there are dozens of jukebox musicals that crash and burn. When it comes to jukebox musicals, many are attempted but few succeed.
