How Stephen Colbert Got His Start In Hollywood

Stephen Colbert, known for his sharp wit and charismatic presence on screen, is equally charming off-camera. Born on May 13, 1964, in Washington, D.C., Colbert was raised in a close-knit Catholic family as the youngest of eleven siblings.

Our story begins in the windy city of Chicago, where Stephen Colbert’s comedic roots were planted. Picture it: the 1980s, a young Colbert sauntering into Chicago’s renowned Second City comedy theater with dreams of making it big. Armed with nothing but a sharp wit and an impressively high energy level, Colbert was ready to charm the pants off audiences—and he did, eventually making them laugh their pants off, too. Rumor has it that his stand-up routine was so engaging, even the furniture was moved to tears.

Colbert’s breakthrough came with the Chicago improv scene. He was like a comedic hurricane sweeping through Second City, bringing with him a whirlwind of characters and skits that could make even the most stoic audience members snort with laughter. His performances were so electrifying that it’s said he once caused a light fixture to short-circuit from sheer comedic intensity. The lampshade wasn’t the only thing that went dark; Colbert’s future was about to be illuminated in the brightest spotlight of all—Hollywood.

The journey to superstardom began in earnest when Colbert joined the cast of 'The Daily Show' in 1997. Here, he honed his signature blend of sarcasm and enthusiasm while brilliantly playing a fictionalized version of himself—a character so convincing that it’s rumored some people tried to hire him as a motivational speaker. Colbert's ability to deliver news with a side of snark and irreverence became his calling card. His on-air persona was so delightfully over-the-top that it practically demanded its own parade.

Fast forward a few years, and Colbert's meteoric rise continued with 'The Colbert Report,' a show where he played an exaggeratedly conservative pundit in the vein of a faux-news commentator.

The show was a hit, becoming a platform for Colbert’s ingenious satire and allowing him to channel his inner buffoon with gleeful abandon. The Colbert character was so convincing that some viewers believed he was the second coming of William F. Buckley—if Buckley had a penchant for slapstick comedy and a love for absurdly grandiose gestures.

As Colbert’s career soared, so did his celebrity status. He was the toast of late-night television, a beloved figure whose sharp humor and sharp suits made him a fixture on the red carpet and in the hearts of fans everywhere. In 2015, Colbert made a historic leap to 'The Late Show with Stephen Colbert,' taking over the iconic slot from David Letterman. The transition was so smooth that it was rumored even the studio lights breathed a sigh of relief.

With 'The Late Show,' Colbert solidified his status as a late-night powerhouse. He became a master of interviewing everyone from politicians to pop stars with the same blend of earnest curiosity and biting wit. His success was so comprehensive that even his detractors were forced to admit—begrudgingly—that Colbert was a force to be reckoned with. His show became a nightly ritual for millions, proving that humor, when wielded with Colbert’s precision, could indeed change the world—or at least make it a lot funnier.

His upbringing in a bustling household imbued him with a deep sense of humor and an appreciation for family life. Colbert’s personal life is marked by his strong bonds with his family, particularly his wife, Evelyn McGee-Colbert, whom he married in 1993. Evelyn, a prominent actress and philanthropist, shares Colbert’s passion for the arts and has often been described as his anchor and confidante.

Together, they have three children, and the Colbert family is known for their privacy and close ties, often preferring to stay out of the limelight and focusing on their shared values and interests. So, here’s to Stephen Colbert—the man who took a dream, a few well-timed punchlines, and an infectious laugh, and turned them into a late-night empire that continues to brighten our evenings with its wit and charm.