I did Shakespeare in the Park lines when I was a college student in NYC, early 2000s. It was a pleasant experience then, and especially if you went early in the run, you rarely had to wait more than a couple hours for tickets. (Often if you went during the first week of performances, you could walk right up around 1pm -- when they started distributing -- and receive a pair with no wait.) As Kad mentioned though, given that summer weather is far less temperate now, the prospect of a multi-hour queue is far less appealing. Also, it's really only conducive to people who live in the city. If you don't have an apartment or hotel where you can nap in the afternoon, you'll be mighty tired once curtain rolls around.
"You travel alone because other people are only there to remind you how much that hook hurts that we all bit down on. Wait for that one day we can bite free and get back out there in space where we belong, sail back over water, over skies, into space, the hook finally out of our mouths and we wander back out there in space spawning to other planets never to return hurrah to earth and we'll look back and can't even see these lives here anymore. Only the taste of blood to remind us we ever existed. The earth is small. We're gone. We're dead. We're safe."
-John Guare, Landscape of the Body