New venue Woodlawn Comedy is opening this weekend in the former Woodlawn Theatre, with its owners promising to bring big laughs and big names to the renovated space.
The operators of the relaunched theater — located at 1920 Fredericksburg Road in San Antonio’s burgeoning Deco District — will christen it with performances by more than 20 local comedians this weekend. The first 500 tickets to Friday’s show are free with 300 already spoken for, they said. The rest of the tickets for Friday’s show, as well as Saturday’s, are going for $10 each.
The rest of Woodlawn Comedy’s calendar is starting to fill up with comedians with enough stature to headline the 1,000-capacity venue on their own, co-owner Shane Quade told the Current.
Comedian Pauly Shore, known ’90s comedy movies including Encino Man and Son in Law, will perform twice on Saturday, April 12 with shows at 7 p.m. and 10 p.m. Tom Cotter, a breakout star from Season 7 of America’s Got Talent, will follow on Saturday, May 3, co-headlining with Last Comic Standing finalist Kerri Louise.
Though venue officials aren’t ready to announce other big names on the way, Quade said some have sold out venues as large as the Majestic Theatre and Frost Bank Center.
“We’re about to release almost our entire May calendar,” he added.
Quade and his partner Keith LaRosa have overseen extensive renovations over the past few months, transforming the former movie house from a 450-capacity venue to one with seating for 985.
The venue is now equipped with wider seats and more room between rows. During shows, guests will be able to order drinks with QR codes they can scan on the seats in front of them. Wait staff will deliver their orders directly.
The Woodlawn Theatre was built in 1945 by John Eberson, the same architect who constructed San Antonio’s Majestic along with other high-profile theaters around the country. That specialty earned him the nickname “Opera House John.” In 1960, another John — John Wayne — hosted the world premiere of The Alamo at the Deco District cinema.
Production company Woodlawn Theatre Inc., which specialized in musicals, took up residency in the venue in 2012. However, it vacated the space in early 2024, when it changed its name to Wonder Theater and relocated to Wonderland of the Americas’ former Santikos Bijou space.
The Woodlawn Theatre has since remained mostly vacant, only hosting occasional one-off events.
Woodlawn Comedy co-owner Keith LaRosa, who plans to relocate to San Antonio from his home in Austin, said the partners have invested close to $1 million in the project, much of that coming from LaRosa’s personal inheritance. His mother also dropped $270,000 on the seats. State-of-the-art lighting and sound, complete with an LED display wall, were another $400,000.
“We’re just dumping everything into this project,” LaRosa said. “But we’re trying to do things differently here.”
Unlike a typical comedy club, there won’t be a two-drink minimum, LaRosa said, adding that he also plans to keep drinks inexpensive.
“Just because you’re going to a concert, there’s no reason to pay $15 for a beer. We’re actually doing normal drink prices,” LaRosa said. “People need to go out and have a good time, and it doesn’t need to break the bank.”
With opening only a few days away, it’s crunch time for completing the renovations.
Some seats are still covered in plastic on the balcony as the crew adds the finishing touches. LaRosa and Quade, along with a small team of workers, will install the lighting this week.
Since renovations began in August, the updates have included gutting the space, replacing air conditioning and addressing complaints of the historic building’s musty smell, according to LaRosa. The auditorium has gotten a fresh coat of paint and holes in the ceiling have been patched.
The stage has also been rebuilt and cut down in size to accommodate more seating. The theater lost its historic designation due to the seating expansion, but LaRosa said the additional capacity is worth it.
LaRosa also had green rooms installed behind the stage for the talent, and a former prop room behind the second-floor balcony is now a second bar fashioned as a speakeasy. Dubbed 1920 Lounge, the space will host the “Laughter Party” — a play on “afterparty” — that LaRosa said will follow the bigger shows. The Laughter Party will feature local comics in the intimate setting.
LaRosa also will handle Woodlawn Comedy’s ticketing through Loop One Inc., a ticketing company he co-owns with Quade. In other words, this isn’t a Live Nation venue.
Woodlawn Comedy is opening in the newly renovated building that once housed the Woodlawn Theatre.
New venue Woodlawn Comedy is opening this weekend in the former Woodlawn Theatre, with its owners promising to bring big laughs and big names to the renovated space.
The operators of the relaunched theater — located at 1920 Fredericksburg Road in San Antonio’s burgeoning Deco District — will christen it with performances by more than 20 local comedians this weekend. The first 500 tickets to Friday’s show are free with 300 already spoken for, they said. The rest of the tickets for Friday’s show, as well as Saturday’s, are going for $10 each.
The rest of Woodlawn Comedy’s calendar is starting to fill up with comedians with enough stature to headline the 1,000-capacity venue on their own, co-owner Shane Quade told the Current.
Comedian Pauly Shore, known ’90s comedy movies including Encino Man and Son in Law, will perform twice on Saturday, April 12 with shows at 7 p.m. and 10 p.m. Tom Cotter, a breakout star from Season 7 of America’s Got Talent, will follow on Saturday, May 3, co-headlining with Last Comic Standing finalist Kerri Louise.
Though venue officials aren’t ready to announce other big names on the way, Quade said some have sold out venues as large as the Majestic Theatre and Frost Bank Center.
“We’re about to release almost our entire May calendar,” he added.
Quade and his partner Keith LaRosa have overseen extensive renovations over the past few months, transforming the former movie house from a 450-capacity venue to one with seating for 985.
The Woodlawn’s stage has been cut down in size to roughly double its seating capacity.
The venue is now equipped with wider seats and more room between rows. During shows, guests will be able to order drinks with QR codes they can scan on the seats in front of them. Wait staff will deliver their orders directly.
The Woodlawn Theatre was built in 1945 by John Eberson, the same architect who constructed San Antonio’s Majestic along with other high-profile theaters around the country. That specialty earned him the nickname “Opera House John.” In 1960, another John — John Wayne — hosted the world premiere of The Alamo at the Deco District cinema.
Production company Woodlawn Theatre Inc., which specialized in musicals, took up residency in the venue in 2012. However, it vacated the space in early 2024, when it changed its name to Wonder Theater and relocated to Wonderland of the Americas’ former Santikos Bijou space.
The Woodlawn Theatre has since remained mostly vacant, only hosting occasional one-off events.
Woodlawn Comedy co-owner Keith LaRosa, who plans to relocate to San Antonio from his home in Austin, said the partners have invested close to $1 million in the project, much of that coming from LaRosa’s personal inheritance. His mother also dropped $270,000 on the seats. State-of-the-art lighting and sound, complete with an LED display wall, were another $400,000.
“We’re just dumping everything into this project,” LaRosa said. “But we’re trying to do things differently here.”
Unlike a typical comedy club, there won’t be a two-drink minimum, LaRosa said, adding that he also plans to keep drinks inexpensive.
“Just because you’re going to a concert, there’s no reason to pay $15 for a beer. We’re actually doing normal drink prices,” LaRosa said. “People need to go out and have a good time, and it doesn’t need to break the bank.”
With opening only a few days away, it’s crunch time for completing the renovations.
Some seats are still covered in plastic on the balcony as the crew adds the finishing touches. LaRosa and Quade, along with a small team of workers, will install the lighting this week.
Renovations began in August, including gutting the theater, painting it and replacing the air conditioning.
Since renovations began in August, the updates have included gutting the space, replacing air conditioning and addressing complaints of the historic building’s musty smell, according to LaRosa. The auditorium has gotten a fresh coat of paint and holes in the ceiling have been patched.
The stage has also been rebuilt and cut down in size to accommodate more seating. The theater lost its historic designation due to the seating expansion, but LaRosa said the additional capacity is worth it.
LaRosa also had green rooms installed behind the stage for the talent, and a former prop room behind the second-floor balcony is now a second bar fashioned as a speakeasy. Dubbed 1920 Lounge, the space will host the “Laughter Party” — a play on “afterparty” — that LaRosa said will follow the bigger shows. The Laughter Party will feature local comics in the intimate setting.
LaRosa also will handle Woodlawn Comedy’s ticketing through Loop One Inc., a ticketing company he co-owns with Quade. In other words, this isn’t a Live Nation venue.
To reel in big acts, the venue has talent buyers in New York and Los Angeles, LaRosa said. The East Coast talent buyer, Eddie Brill, is a comedian who booked for The Late Show with David Letterman and performed as the show’s warm-up comic. The buyer in Los Angeles, Elizabeth Reilly, is a Sunset Strip veteran and comedian who’s also booked tours for stand-up Ahmed Ahmed, according to LaRosa.
The buyers’ mission, LaRosa explained, is to convince the biggest names in comedy to add San Antonio to tours that otherwise might skip the city due to booked-up calendars at venues including the Majestic, Stable Hall or the Aztec Theatre.
LaRosa said he envisions tickets for larger comedy shows falling in the $30-to-$50 range, with almost all of that money going to the talent. The venue will make its money at the bar, he added. While larger shows will have assigned seating, audience members can choose their own seats for the local shows on a first-come-first-served basis.
Other than comedy, LaRosa said the venue will host occasional sit-down concerts, TED Talk-stylized events and even an upcoming Bitcoin conference.
