The 90s Skit Where Jerry Seinfeld Goes To Jail Might Be The Funniest SNL Video Ever
'Seinfeld' meets 'Oz'.
Entertainment
March 24, 2023

Back in 1999, Saturday Night Live blessed us with a hilarious mashup of two 90s TV shows.

The skit sees Jerry Seinfeld shipped off to jail where he starts mingling with the characters from fellow 90s show Oz, including Tobias Beecher, Vernon Schillinger, Ryan O’Reily and Augustus Hill, all played by their actual actors, Lee Tergesen, J. K. Simmons, Dean Winters and Harold Perrineau.

Beginning with a voice-over and opening crawl, the narrator describes: “On May 14th 1998, Jerry, George, Elaine, and Kramer were sentenced to one year in prison for violating the Massachusetts Good Samaritan Law.”

“Then, due to a series of sarcastic quips Jerry made to prison guards, and a series finale regarded by most TV critics as “Satisfactory At Best”, Jerry Seinfeld was transferred to a maximum security prison. That facility is known as…[cut to title card: “OZ”].”

The skit goes on to see Jerry flossing and working out while the other inmates engage in everyday jail shenanigans (getting freaky, planning to jump each other, etc). Initially sticking out like a sore thumb, Jerry gossips his way to friendship, before he and the other inmates make a bet to see who can “hold out” the longest.

Relive the iconic sketch in its entirety below.

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