If you've only experienced theatrical productions inside the theme parks, you're working with an incomplete picture of Orlando. The city has a full-scale performing arts infrastructure downtown, and it's better than most people who've never been would guess.
Dr. Phillips Center
The Dr. Phillips Center for the Performing Arts on Magnolia Avenue opened in 2014 and completely changed what was possible in Orlando. The 2,700-seat Walt Disney Theater handles Broadway touring shows. Then there's Steinmetz Hall - one of the most acoustically advanced concert halls built in the last decade, a room specifically engineered for sound in a way that most cities don't bother with. The programming covers Broadway, symphony, dance, and genre concerts at a consistent level of quality.
Broadway season runs September through May. Pre-theater: Capa on the 17th floor of the Four Seasons across the street does a strip steak with peppercorn butter that's worth the splurge. Walk down to the theater from there and feel appropriately fancy about it.
The Park and the Peculiar
Orlando Shakespeare Theater in Loch Haven Park does both Shakespeare and contemporary drama - they're not just running the safe, familiar productions but genuinely interpreting the work. The campus sits next to the Orlando Museum of Art and the Science Center, so you can build a full afternoon in the park before a show.
Blue Man Group has a permanent home at Universal Orlando and is worth seeing at least once - part performance art, part comedy, part concert, and genuinely unlike anything else. Loud, weird, and fun in a way that defies easy description. Just go.
Stand-Up Scene
Orlando Improv on International Drive books national touring headliners in a proper two-drink-minimum club setup - reliable, well-run, and the place to be when a comedian you know is in town. SAK Comedy Lab downtown has been the city's improv institution since 1991, doing long-form work in a more theater-forward format. Check the listings for both on any given weekend. Grab tickets on Evil Tickets and catch something worth the drive.