The Rat Pack Lounge
Come swing, sing and savor the days of highballs and high rollers!
The Winter Park Playhouse
711 N Orange Ave Winter Park, FL 32789 Get Directions
Additional Dates
- September 24th at 7:30 pm
- September 25th at 2:00 pm
- September 25th at 7:30 pm
- September 26th at 2:00 pm
- September 26th at 7:30 pm
- October 1st at 2:00 pm
- October 2nd at 2:00 pm
- October 2nd at 7:30 pm
- October 3rd at 2:00 pm
- October 3rd at 7:30 pm
- October 4th at 2:00 pm
- October 8th at 2:00 pm
- October 9th at 2:00 pm
- October 9th at 7:30 pm
- October 10th at 2:00 pm
- October 10th at 7:30 pm
- October 11th at 2:00 pm
- October 15th at 2:00 pm
- October 16th at 2:00 pm
- October 16th at 7:30 pm
- October 17th at 2:00 pm
- October 17th at 7:30 pm
- October 18th at 2:00 pm
Swing Back to the Era of Cool: “The Rat Pack Lounge” at Winter Park Playhouse
Get ready to step into a world of fedoras, highballs, and pure showbiz magic. The Winter Park Playhouse is set to host The Rat Pack Lounge, a delightful musical comedy that reunites the legendary trio of Frank Sinatra, Dean Martin, and Sammy Davis Jr. for one unforgettable night.
The Story
After the Rat Pack leaves some unfinished business on Earth, God sends Frank, Dean, and Sammy back for one night to make things right and fulfill a promise to the owner of the Rat Pack Lounge. What follows is a heavenly mix of comedy, camaraderie, and toe-tapping nostalgia as the icons take the stage once more.
This isn’t just a concert — it’s a full theatrical experience packed with the smooth charisma, sharp humor, and signature style that made the Rat Pack legends.
The Music
Audiences will be treated to more than 30 of the Rat Pack’s greatest hits, including timeless classics such as “My Way,” “Come Fly with Me,” “Ain’t That a Kick in the Head,” “Everybody Loves Somebody Sometime,” and many more swingin’ favorites that defined an era.
Written by James Hindman and Ray Roderick, with musical arrangements by John Glaudini, the show captures the golden age of cool with infectious energy and heart.
The Venue & Season
The Rat Pack Lounge runs September 25 – October 18, 2026, with previews on September 24 & 25. It’s part of the Winter Park Playhouse’s 2026–27 season — their first full season in the beautifully renovated theater at 711 N Orange Avenue in charming Winter Park, Florida.
The intimate venue features tiered seating and improved accessibility, making it the perfect setting for an up-close-and-personal night with these icons.
Performance Schedule & Tickets
Regular performances include evening shows on Fridays and Saturdays, plus matinees on Saturdays, Sundays, and select Thursdays. Preview tickets are offered at a discount, and pricing ranges from $20 (students 15+, military, industry) to $52 for adults, with senior discounts available. Groups of 10+ receive special rates.
Recommended for ages 15 and up.
Whether you’re a lifelong Rat Pack fan or discovering their magic for the first time, The Rat Pack Lounge promises an evening of laughter, nostalgia, and world-class entertainment that will have you singing along and savoring every moment.
Mark your calendars for September 25 – October 18, 2026, and get ready to swing! Tickets and more information are available at winterparkplayhouse.org.
Come for the music. Stay for the magic. The Rat Pack is back in town.