Stephen Colbert’s eleven-year run as the host of *The Late Show* has been characterised by an impressively entertaining blend of humour and star power, culminating in memorable moments that have highlighted the show’s whimsical nature. Tonight marks the end of an era as the acclaimed comedian wraps up his tenure on CBS, a journey filled with laughter, surprises, and an impressive lineup of celebrity guests.
:max_bytes(150000):strip_icc():format(jpeg)/stephen-colbert-show-michael-keaton-052026-4215d14ed6444dc7805fbdcb4d70a295.jpg)
Over the years, Colbert has welcomed a host of A-listers to his stage, creating a unique setting where even some of the world’s most recognizable faces have stepped outside their typical personas. From former President Barack Obama to Hollywood icons like Kate Winslet and Will Ferrell, Colbert has demonstrated an unparalleled ability to engage guests in amusing and often absurd situations that delight audiences.
Among these notable interactions was a playful moment in 2016 when the former President participated in a game of wastepaper basketball. The light-hearted competition revealed Colbert’s knack for mixing politics with comedy. In a similar vein, Winslet joined Colbert in a delightful re-imagining of a scene from *Titanic*, where they addressed the longstanding debate over whether her character Rose and Jack could have shared a door to survive.

Another memorable instance featured Michelle Obama, who participated in Colbert’s “Blanket Fort” skit, bringing a touch of her own charm to the comedic premise that captivated the audience in 2016. This dynamic interaction is emblematic of how Colbert has often been able to transform moments of seriousness into laughter, transcending the usual late-night format.
Colbert’s playful approach is evident through his interactions with actors like Will Ferrell, who, in 2016, attempted to take on the role of an exotic animal expert, amusingly presenting fictitious creatures such as a “short-spine Peruvian mongoose.” This absurdity, along with other skits featuring guests like Aubrey Plaza, provided a fresh and often silly dialogue, making *The Late Show* a platform for unpredictable and lighthearted entertainment.

In 2018, the show highlighted Colbert’s ability to foster genuine connections with his guests. Jennifer Lawrence, known for her playful demeanor, brought a sense of fun to her segment as she kicked off her shoes and got comfy, displaying a candid side that resonated with viewers. Similarly, Liv Tyler, during her appearance later that year, indulged Colbert’s enthusiasm for *Lord of the Rings* by bringing a replica sword, allowing for an impromptu skit that delighted fans of the franchise.
Colbert’s spontaneity often led to thrilling performances. Notably, his duet with Jennifer Hudson in 2019 showcased his willingness to share the spotlight while holding his own beside a powerhouse vocalist. Performances like this underscored the show’s commitment to celebrating talent, elevating both the host and his guests in the process.
As the curtain falls, the final episode tonight promises to encapsulate the essence of *The Late Show* and the camaraderie that developed over the years. Special segments have highlighted not only celebrity antics but also moments of genuine emotion, as seen when Colbert engaged in thoughtful discussions with guests like Julia Louis-Dreyfus about life’s bigger questions.
The legacy that Colbert leaves behind is one of laughter, creativity, and a genuine approach to entertainment that endeared him to audiences. In a touching culmination, his past guest and predecessor David Letterman made an appearance earlier this month, symbolising the connection between late-night hosts and the tradition of laughter they embody.
In reflecting on his journey, Colbert has noted plans for the day after the series concludes—an informal hint at possible new adventures that await him, likely involving a good dose of merriment. With a fond farewell, *The Late Show* will leave a lasting mark on the landscape of late-night television, with Stephen Colbert at the helm for a remarkable chapter filled with laughter and whimsy.
