One thing about us Clevelanders is we know how to take (and make) a joke. With the Rock & Roll Hall of Fame’s new exhibit, “SNL: Ladies & Gentlemen… 50 Years of Music,” now is the perfect time to talk about comedy in The Land — specifically, the big-name comics who once called Cleveland home.
Bob Hope, one of the most legendary comedians of all time, spent his formative years in Cleveland, Ohio, after his family emigrated from England in 1908, and was even a minority owner of the Cleveland Guardians for 40 years. The comedian, actor and television personality gained widespread recognition for his television specials and stand-up comedy, with his “Bob Hope Christmas Special” becoming a holiday tradition. However, it was his countless USO shows during wartime that truly cemented his place as a beloved national figure, bringing laughter to troops around the world. In Hollywood, he starred in over 70 films and became a regular at the Academy Awards, hosting the ceremony 19 times — more than anyone else in history.
Tim Conway, known for characters like "The Old Man" and "Mr. Tudball" on “The Carol Burnett Show,” was born in 1933 in Willoughby, Ohio. A proud member of Phi Delta Theta at Bowling Green State University, Conway got his start in comedy on the radio before Rose Marie discovered him. He became a comedic legend with five Primetime Emmy Awards, a Golden Globe and a star on the Hollywood Walk of Fame (because, of course). And if that wasn’t enough, he was inducted into the Television Hall of Fame in 2002, proving that laughter really does keep you young.
Phoebe Robinson, born in 1984 in Bedford Heights, Ohio, left home in 2002 to study screenwriting at Pratt Institute in New York City. She co-created and co-starred in the hit podcast-turned-HBO series "2 Dope Queens," and has hosted other acclaimed podcasts like "Sooo Many White Guys.” Robinson has written and acted in projects like "Everything’s Trash" and "BoJack Horseman," and performed on "Late Night with Seth Meyers." Her third book, "Please Don’t Sit on My Bed in Your Outside Clothes," became a national bestseller and launched Tiny Reparations Books, which supports writers of color. Recently, she signed a first look deal with Sony Pictures Television. At this point, we're convinced she can do it all.
The “Superstar” herself, Molly Shannon, hails from Cleveland and is best known for her iconic stint on “Saturday Night Live.” There, she became a household name with unforgettable characters like the awkward Catholic schoolgirl “Mary Katherine Gallagher” and the energetic 50-year-old “Sally O'Malley,” who likes to “kick, stretch and kick.” Her work on SNL earned her widespread acclaim and a beloved place in comedy history. Shannon’s film career includes starring roles in “Superstar” (based on her SNL character), “Never Been Kissed” and “Wet Hot American Summer.” Beyond the big screen, she’s showcased her comedic range in TV shows, most recently joining Hulu’s “Only Murders in the Building.”
Born in 1956 in Cleveland, Arsenio Hall earned his communications degree from Kent State University before becoming a comedian, actor and television host. After relocating to Chicago in 1979, he launched his stand-up career and opened for legends like Aretha Franklin and Tina Turner. Best known for his iconic "woof, woof!" catchphrase, "The Arsenio Hall Show" became a groundbreaking late-night hit, bringing multicultural flair to late-night TV. Hall also starred alongside Eddie Murphy in "Coming to America" and its 2021 sequel, "Coming 2 America." As one of the first Black late-night hosts, Hall’s humor, charisma and advocacy for diversity made him a lasting figure in entertainment.
Another Kent State University attendee, Steve Harvey grew up in Cleveland . In 1985, he was selling insurance when he took a leap of faith and won an amateur night contest at a local comedy club. That win changed everything, and Harvey turned his focus to stand-up comedy, eventually becoming an Emmy Award-winning comedian, actor, author and television host. Best known for hosting “Family Feud” and starring in “The Steve Harvey Show,” he’s also starred in countless films like “Think Like a Man” and made a name for himself as a motivational speaker. With seven Daytime Emmy Awards, two Marconi Awards and 14 NAACP Image Awards under his belt, we’re pretty sure his shelves are starting to sag.
Shaker Heights-born Fred Willard was a master of comic timing and improvisation. He gained fame for his role as the lovably dimwitted sidekick Jerry Hubbard on "Fernwood Tonight." With over 100 appearances on "The Tonight Show with Jay Leno," Willard became known for his quick wit and ability to turn any character into a comedic standout. His extensive career also included memorable roles in "Modern Family," "This Is Spinal Tap" and "Best in Show."
Vanessa Bayer, born in Orange, Ohio, is a comedian, actress and writer best known for her six seasons on "Saturday Night Live." She earned widespread recognition for her impressions, including her iconic portrayal of Miley Cyrus and her famous Weekend Update character Jacob the Bar Mitzvah Boy. Bayer has also starred in the hit series "I Love That for You" and appeared in films like "Trainwreck" and "The To Do List." With her sharp comedic timing and versatility, Bayer continues to shine in both TV and film, leaving her mark as one of the most talented performers in comedy today.
Drew Carey, a proud Cleveland native, is best known as the star of “The Drew Carey Show” — set right here in Cleveland — and as the longtime current host of “The Price Is Right.” Born and raised in Old Brooklyn, Carey has always worn his hometown pride on his sleeve. This former Marine got his big break after killing a set on his Tonight Show debut. He’s also beloved for his quick wit as the host of “Whose Line Is It Anyway?” and continues to represent Cleveland with heart, humor and loyalty.
David Wain is a Cleveland-born writer, director, actor and comedian known for his offbeat humor and cult-classic comedies. A graduate of Shaker Heights High School, Wain got his start with the sketch comedy troupe “The State” before going on to co-create “Wet Hot American Summer” and direct films like “Role Models” and “They Came Together.” His unique comedic voice and creative legacy continue to make Cleveland proud.
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