{"id":206159,"date":"2026-03-25T23:49:13","date_gmt":"2026-03-25T23:49:13","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-fl\/206159\/"},"modified":"2026-03-25T23:49:13","modified_gmt":"2026-03-25T23:49:13","slug":"winter-park-playhouse-closes-their-orlando-shakes-residency-with-a-kevin-kelly-cabaret","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-fl\/206159\/","title":{"rendered":"Winter Park Playhouse closes their Orlando Shakes residency with a Kevin Kelly cabaret"},"content":{"rendered":"

\"KevinKevin Kelly Credit: photo courtesy of the artist<\/p>\n

Over the past quarter-century, Kevin Kelly<\/a> has become one of Central Florida\u2019s most celebrated crooners by effortlessly transporting audiences back to the era of Bing Crosby, Bobby Darin and Frank Sinatra. This week, on March 25 and 26, Kelly cranks up his musical time machine again with On the Atchison, Topeka and the Winter Park Stage, the latest in his long-running series of cabarets for Winter Park Playhouse<\/a> and the final WPP show to premiere in their temporary home at Orlando Shakes before they return to their renovated Orange Avenue HQ.<\/p>\n

The youngest of five children, with a minister for a father, Kelly began playing piano and singing in church at an early age. \u201cEverybody played some kind of instrument at some point in their lives, so I think I got bit very young,\u201d says Kelly. \u201cI just liked being on stage.\u201d<\/p>\n

Even though he moved into secular music during college at Kansas State University, his family remains supportive and have unexpectedly showed up for his shows, from Bent to Grease. \u201cMy favorite moment is, when I did Pump Boys and Dinettes years ago, my father snuck in a little recorder, and he just held it in his coat and recorded the show because I was doing country music and he was a huge country music fan,\u201d Kelly recalls. \u201cSo that little cassette sat behind his desk forever.\u201d<\/p>\n

After a post-college stint as music director of a small theater company in Newport, Rhode Island, Kelly came to Orlando in 1997 seeking escape from northern winters and lived on Kirkman Road [full disclosure: with my wife\u2019s college roommate] while working full-time as a character coordinator and scheduler backstage at Walt Disney World.\u00a0<\/p>\n

\u201cI\u2019d stopped performing. There was actually about a 10-year period where I didn\u2019t sing, didn\u2019t play [music], I didn\u2019t do anything,\u201d he says. \u201cIt was soul-crushing. I said, \u2018I\u2019ve gotta do this, because it\u2019s what I do.\u2019\u201d<\/p>\n

After getting cast by Katrina Ploof for a reading at Shakes, Kelly was hired by Mad Cow\u2019s Alan Bruun to play John Wilkes Booth in Sondheim\u2019s Assassins, which coincided with him leaving Disney. Aside from an abortive outing as an Ollivanders wandkeeper when Universal\u2019s first Harry Potter land opened \u2014 \u201cThis kind of nitpicky corporate theater really isn\u2019t for me, so I walked out of that shift and I never went back,\u201d he says \u2014 Kelly has largely worked under contract for Winter Park Playhouse, making him one of the relatively rare Actors Equity union members making a living in Orlando outside the theme parks.\u00a0<\/p>\n

\u201cI held out for a long time only because companies would rather hire a non-Equity [performer] because it\u2019s less expensive, so I feel like that actually did allow me to book a little more,\u201d Kelly says. \u201cBut as I got older \u2026 I thought, I\u2019m getting of a certain age, and I need to really start thinking about insurance and all that stuff. So that was the big impetus for me, and I\u2019m happy to to be a part of the union.\u201d<\/p>\n

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\n\t\t\t\t\tAfter months of uncertainty, the playhouse will remain in the space it has called home for 23 years\t\t\t\t<\/p>\n

Although he\u2019s starred in many scripted shows for Winter Park Playhouse since first getting cast in Golf: The Musical over 15 years ago, he says cabaret is his favorite format for entertaining \u201cbecause you\u2019re free. You don\u2019t have to be a character; you\u2019re just you. I get to sing songs that I love \u2014 that I connect with \u2014 and tell stories [and] stupid jokes [that] make the audience groan. \u2026 Especially now we\u2019ve got so much on our minds, weighing us down day by day with the news and social media and stuff, so I just really strive to keep everything fun and light.\u201d\u00a0<\/p>\n

When asked how he develops his cabarets, Kelly confesses, \u201cI always have good intentions, and I always think, \u2018Oh, God, I\u2019m going to do some kind of theme.\u2019 [But] nine times out of 10, I get all my songs on little 3-by-5 cards [and] shuffle them around until I get the combination I like. And then I just kind of build it around the songs.\u201d He says his latest show was scrapped and rewritten from scratch in just four weeks: \u201cIt may be kind of a mishmash of songs, it\u2019s always kind of an organized chaos, but that\u2019s what I enjoy.\u201d<\/p>\n

For this outing, Kelly is once again accompanied by keyboardist Chris Leavy, his frequent collaborator and a WPP fixture. \u201cWe\u2019ve done so many of these shows together, we joke that I can send him a song list and I\u2019ll see you the night of the show, because after working so much together we know how each other works. I can literally just turn and look at him and he\u2019ll know that I have no freaking clue what song is coming next,\u201d says Kelly. \u201cHe is one of the most beautiful minds in in this town, so talented, such a treasure trove of information.\u201d<\/p>\n

Winter Park Playhouse is scheduled to cut the ribbon for their newly rebuilt home on July 7, beginning their season in August on an expanded stage with additional breathing room behind the curtain, which should make quick changes more comfortable. But one thing that shouldn\u2019t change is the feeling that has made WPP an anchor of the theater community.\u00a0<\/p>\n

\u201cI\u2019ve always found that Winter Park Playhouse is a very warm and very family-oriented kind of atmosphere,\u201d says Kelly. \u201cMeaning that when you start working for them, you become part of their family.\u201d<\/p>\n

Kevin Kelly, \u201cOn the Atchison, Topeka and the Winter Park Stage\u201d: 7 p.m. Wednesday and Thursday, March 25-26; Mandell Theater, Lowndes Shakespeare Center,\u00a0812 E. Rollins St.; 407-645-0145; winterparkplayhouse.org<\/a>; $23<\/p>\n

Orlando\u2019s daily dose of what matters. Subscribe to The Daily Weekly.<\/p>\n

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\n\t\t\t\t\tPlus plenty more Orlando food events and restaurant openings\t\t\t\t<\/p>\n

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\n\t\t\t\t\t\u201cSome people are like, \u2018Do you really think that doing something will do anything?\u2019 And I\u2019m like, \u2018No, but I know that not doing anything will do nothing.\u2019\u201d \t\t\t\t<\/p>\n

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This article appears in March 25-31, 2026<\/a>.<\/p>\n

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