City Winery Pittsburgh brings world-class comedy to the Strip District, and Pittsburgh crowds bring exactly the energy that great stand-up deserves — real, unpretentious, and ready for a night they won't forget. Our comedy shows in Pittsburgh draw top touring comedians and breakthrough voices to one of the most intimate live entertainment venues in the city, where every table has a great sightline and no one's too far from the stage to catch every expression and every perfectly delivered punchline. Add a full dinner menu and an award-winning wine program and you've got a Pittsburgh night out that's genuinely hard to beat. Beyond comedy, explore our full Pittsburgh events calendar including Pittsburgh rock, Pittsburgh R&B, Pittsburgh jazz, and Pittsburgh brunch, all paired with dinner service and award-winning wines. Whether you're a longtime Pittsburgh comedy fan or just looking for something different to do in the Steel City, City Winery delivers. Browse upcoming Pittsburgh comedy shows and make a night of it in the Strip District.