I am now here to tell you that someone has done exactly this, and that the result is, to apply an over-used but apt modern superlative, awesome -- and I use that term in its classic sense, of "something which inspires awe". I should add that where theater is concerned, I am not easy to awe. Specifically, the librettist for Head Over Heels is Jeff Whitty, perhaps best known as the father of the Tony-winning Avenue Q, which may go some way toward explaining why this show actually works.
I'm not even going to try to explain the plot (such as it is), except to observe that it is (a) in the broad general neighborhood of Shakespeare's more convoluted comedies and late romances -- it is perhaps not a coincidence that OSF is also producing Pericles Prince of Tyre this year -- and (b) also in the broad general neighborhood of the two stage adaptations of classic Marx Brothers movies OSF has produced recently. What's of greater importance is the degree to which the show doesn't merely play with the metaphorical "fourth wall", but gleefully tunnels right through it into the audience. And that's no metaphor -- John Tufts, as a classic Shakespeare-league Fool crossed with the Leading Player in Pippin (and this show's nominal master of ceremonies), spent part of the intermission strolling through the house, plopping briefly down in one of the best seats in the theater while talking casually to various audience members. At least half the cast began the evening by stationing themselves at intervals throughout the aisles several minutes before curtain time; I realized this when I looked up from my playbill, noticed an eight-foot pool of purple skirt stretched across the concrete behind me, and realized that the animated (and entirely off-the-cuff) conversation I'd been overhearing from the next row back was taking place between one lady in the aisle seat and one of the principal female players.
And it only got wilder from there. When curtain time did arrive, Tufts strode out to center stage and introduced himself -- both as himself and as his character -- then went on to do the same for several of the leading performers. Then there was the Oracle of Delphi, who admitted that her gift of prophecy was made possible because she was reading ahead in the script. (Yes, Dr. Teeth and the Electric Mayhem got there first in the original Muppet Movie, but Whitty and the Oracle -- later to be known as Linda -- promote the shtick from an amusing throwaway gag to a key plot and thematic point near the climax.)
What prompts the occurrence of awe, though, is that all of the Shakespeare-grade romantic foolery (including lots of gender-bending) and fourth-wall insanity is wrapped in a 24-karat Rock Musical soundtrack. As I noted earlier, this was my very first encounter with Go-Gos music, and while '80s girl-group rock is not at all my usual beat, it was impossible not to be drawn in by the energy and vigor of the songs. My only frustration is that the enthusiasm of the orchestra occasionally overrode the vocals during musical numbers, making it difficult to make out lyrics, but that was only an intermittent issue.
Verdict? If you are a fan of any one subset of the source material (Whitty, Philip Sidney, Shakespearean comedy, rock musicals, etc.), this is a must-see. And there may be a bonus bit of off-the-wall resonance for the genre-fiction fans in the gallery. It occurs to me that Head Over Heels -- and the Go-Gos sound -- blends '80s rock and fantastical elements in a way that fans of Seanan McGuire's music may find especially appealing. And in the reverse context, one of the more memorable performances in the show -- the role of Princess Pamela -- comes from actress Bonnie Milligan, whom I'd argue is a passable ringer for Seanan....