Saturday Night Live: the best and worst musical hosts

Published on April 6, 2026

This weekend, Chance the Rapper will take the stage to host Saturday Night Live, with Eminem serving as the musical guest. Last weekend, Taylor Swift graced the late-night sketch institution, performing a couple of songs, but she also handled full hosting responsibilities back in 2009. Since Paul Simon emceed the second-ever episode back in 1975, SNL has provided adventurous musicians the chance to step outside their comfort zones and try their hand at sketch comedy.

Episodes hosted -professional actors can often be a gamble. There are few experiences more cringeworthy than watching a well-meaning celebrity stutter through a commercial parody. Yet, musicians seem to possess a distinct advantage, usually channeling their natural stage presence into a more structured format. However, when they falter, the missteps can be especially glaring.

Over the course of Saturday Night Live’s long history, various musical artists have left a lasting impression—both positive and negative. Some have successfully blended their musical talents with comedic timing, while others have struggled to find their footing under the pressure of live television.

Artists like Justin Timberlake and Billie Eilish have made successful transitions from music to comedy, effortlessly engaging with the sketch material while showcasing their genuine flair for entertainment. Timberlake, in particular, has become a fan-favorite host, known for his infectious energy and quick wit. Eilish has also impressed audiences with her ability to embrace the ridiculousness of sketches while incorporating her unique musical style into the show.

Conversely, there have been instances when musical guests have bombed spectacularly. Experiences like Ashlee Simpson’s infamous lip-sync flub left a stain on SNL’s reputation for live authenticity, showcasing the risks involved when music stars step into the variety show realm. Other artists, although talented musically, struggled with the demands of comedic acting, leading to unmemorable and awkward performances.

As Chance the Rapper prepares to host this weekend’s episode, he faces the dual challenge of delivering laughs while maintaining the musical artistry that has garnered him acclaim. The audience will undoubtedly be eager to see if he can follow in the footsteps of those who have succeeded or learn from those who have stumbled.

As musical guests continue to navigate the unpredictable waters of Saturday Night Live, the distinction remains clear: there are great rewards in taking the plunge, but the risks can be equally high. Whether paving the way for future musical hosts or solidifying their own place in the SNL legacy, the stage is set for Chance to make an unforgettable mark.

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