Wow! When I realized what was going on in this grid I almost couldn't believe it. I haven't made any puzzles yet, so I don't know for sure how tough something like this would be, but it sure impressed me.
Here's how our solve went. The middle fell fairly easily, and the revealer, DOUBLEFEATURE (14D: Drive-in theater draw... with a literal hint to 4- and 21-Down), seemed straightforward enough. Almost too straightforward. I thought, well, the other two long clues will be movies, and it'll be like a double feature. I don't know many Jack Lemmon movies, but I figured "The Odd Couple" was a good bet, and it fit, so in it went. Sinatra, well, let's see, what'd he win that oscar for? "From Here to Eternity?" Too long...
So over the puzzle went to the old movie buff, Frannie. I told her I thought something was fishy, because I couldn't verify "The Odd Couple" with much, and I had absolutely nothing over on the Sinatra side. Using another old movie reference, Frannie broke it. Well, we did, but she started it. She said that 22A: Captain von ____ (musical role) just had to be TRAPP, and suggested THEAPARTMENT as another possible Lemmon movie. (Who knew?) Right then I realized what was happening, and I had her put double Ps into that square. I then also felt confident enough to put in KAR[EN] for 51A: ____ Carpenter. Once freed up to lengthen ( - and by the way, 1A: One of the three dimensions (LEN[GT]H) was devious, because both "width" and "depth" fit in without the rebus!) all the answers, we eventually had enough to guess GRUMPYOLDMEN.
On the East side, it was all up to Frannie, because I couldn't come up with any other Sinatra roles. One of the first she thought of was OCEANSELEVEN, which turned out to be perfect, because it was the first of the two, and entering the rebuses after that was easier than if we had had to erase first letter every time. Okay, maybe that comment is just for electronic solvers. Nevermind if you solve on paper. And if you do, I pity you. I can't imagine the mess that would have arisen from me putting in "The Odd Couple" in pen. Egad! What would Felix have said?
Anyway, this was fantastic. One of the best of the year, in my opinion. Sure, the NW had LBS, EEO (?) and NAS, but I'm giving a LOT of leeway to Mr. Blindauer for this trick. And really, much of the rest was also interesting and/or funny. How 'bout that clue for STROHS (45D: Brew whose name is an article of clothing when read backward)?! I almost think he, too, must have spent time in Wisconsin in a campus bar, where such an insight might just come to you after drinking that cheap beer. And I loved 55D: You may be fooled at its beginning (APRIL). There's bonus fill, too, with OSCARS (48D: Star-studded show, with "the").