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.”
The Jerry Seinfeld in Oz SNL skit is my favorite of all time
— Big E (@Chairistotle) March 28, 2012
“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.