Kevin Webb

Trap Door credits

Acting
  • Mother Courage and Her Children (Original and Repertory run)
  • The Pragmatists (Chicago and Poland tour)
  • Princess Ivona 
  • Decomposed Theatre, Episodes 4 & 6
  • Reality Theatre
  • The Killer
  • The Resistible Rise of Arturo Ui
  • The Duchess of Malfi 

Kevin Webb (he/him/his) has been working onstage at Trap Door since 2016. He is the recipient of Jeff Awards for Sweeney Todd (Principal – Musical) and Into the Woods (Ensemble – Musical). Kevin has several additional Jeff nominations including 3 for Trap Door productions (1 Supporting and 2 Ensemble). He was also featured in Newcity’s Players of 2025 list. When not onstage, you can most likely find Kevin walking dogs around the city or watching horror films in his home. Kevin holds a Master of Music degree from Roosevelt University, CCPA. kevinwebb.org

Gallery

Kevin Webb is a standout. Webb not only reminds us that villainy can exist in even the most cherubic forms, but he also showcases a pleasing tenor singing voice….

Tom Lawler, The Fourth Walsh (about The Duchess of Malfi)

Casey Chapman and Kevin Webb also give standout turns…Webb unearths the oozing black pustule at the center of his [character].

Alex Huntsberger, Time Out Chicago (about The Resistible Rise of Arturo Ui)

Kevin Webb as Edouard, besides being delightfully creepy, does a particularly good job of taking the repetitive, meaningless prose and thrusting some logic into it with flair, and as a result he elicits most of the show’s genuine laughs

Aaron Lockman, PerformInk (about The Killer)

Kevin Webb, in a finely-honed performance that stays just this side of going too far over the top.

Kerry Reid, Chicago Tribune (about The Killer)

Webb steals his scenes. Laughter is almost instinctual as his madness oozes off the stage. Just as in life we are altogether uncomfortable with those individuals we cannot label as good or bad. Such is the case with Webb. Whether we are to cheer for him or against him, who’s to say, it’s impossible not to at least cheer at him.

Amanda Finn, Footlights (about The Killer)

Kevin Webb as Lord Chamberlain delivers a masterful performance of an arch toady who camouflages his brilliance and manipulates his superiors into becoming their darker selves.

Angela Allyn, Chicago Stage and Screen (about Princess Ivona)

Kevin Webb is very fun as the prissily scheming Lord Chamberlain (with a weird glove fetish)

Scott C. Morgan, Windy City Times (about Princess Ivona)

All the performers are marvelous—particularly the leads, Webb and Surney, who are absolutely convincing in pursuit of something unclear.

Mary Wisniewski, NewCity Chicago (about The Pragmatists)

the Swedish cook, portrayed by Kevin Webb in a standout performance (that features his enchanting singing voice).

Julia W. Rath, Around the Town (about Mother Courage and her Children)