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Saturday Night Live: What is SNL's Greatest Season? →

Which season of Saturday Night Live was the greatest of all time? In this episode of High and Low Retrospective, we go deep into the season that redefined late-night sketch comedy—featuring a legendary cast, breakout sketches, cultural moments, and a creative high point that hasn’t been matched since.

Was it the era of Eddie Murphy’s superstardom? The rise of Will Ferrell and Tina Fey? Or maybe the early days of Bill Murray and Gilda Radner? We break down: - The cast that made it iconic - The cultural and political backdrop - The sketches that still live rent-free - And why this season still resonates decades later.

Whether you grew up watching live or caught the reruns on Comedy Central, this is the definitive retrospective on the season that made SNL unmissable.

Don’t forget to like, comment with your favorite cast or sketch, and subscribe for more deep dives into the pop culture moments that shaped us.

Binge-watch the full playlist

Videos to watch:

In Living Color: The Most Dangerous Sketch Show of the 90s https://youtu.be/8D40hjYzOG0

Dave Chappelle's Masterpiece: The Gift and Curse of Chappelle's Show https://youtu.be/c-hHr6YG2Gw

Key & Peele: The Sketch Comedy Show That Won’t Fade https://youtu.be/wPuoNUL3uZU

tags: Saturday Night Live, SNL greatest season, best SNL cast, SNL history, SNL 2008 season, Kristen Wiig, Bill Hader, Tina Fey, Amy Poehler, Andy Samberg, 90s SNL, 2000s SNL, SNL sketches, SNL nostalgia, SNL retrospective, High and Low Retrospective, nostalgic pop culture, sketch comedy history, Lorne Michaels, classic SNL moments, pop culture deep dives, iconic SNL seasons, retro TV shows, comedy history, cultural commentary, YouTube retrospectives
categories: TV shows, Retrospective, Nostalgia
Tuesday 10.28.25
Posted by Vonn+Abrahamm
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