Nick revisits one of the most uneven and troubled years in Saturday Night Live history — Season 23. On paper, it should have been great: a powerhouse cast featuring Will Ferrell, Jim Breuer, Chris Kattan, Molly Shannon, Cheri Oteri, and Tim Meadows, plus the first season with Tina Fey on the writing staff. But instead, the year was marred by misfires, controversy, and heartbreaking loss.

There were dreadful episodes — Sylvester Stallone flopped, Jon Lovitz coasted, Rudy Giuliani was exactly what you’d expect, and audiences were left wondering who Roma Downey was. The deaths of Chris Farley and Phil Hartman cast a long shadow, and Norm Macdonald’s firing over his O.J. Simpson jokes only deepened the chaos.

Still, bright spots broke through the gloom. Nick highlights the funniest sketches of the season, including Helen Hunt’s great monologue with a surprise guest, a classic Mary Katherine Gallagher moment, a hysterical Celebrity Jeopardy featuring David Duchovny’s spot-on Jeff Goldblum, and the debut of Tim Meadows’ The Ladies Man.

A messy, emotional, and unforgettable chapter in SNL’s long history. [Ep 147]