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Talk about simpler times: 20 years ago, Jon Stewart opened the 2002 Grammy Awards with an extended opening monologue joke about ... airport security. But never let it be said that the comedian and former Daily Show host slacks off when it comes to amusing the audience. Stewart almost went the full monty during the two-minute bit, which saw him being stripped down to his boxers by overzealous Grammy security staff.
Watch Jon Stewart's 2002 Grammy monologue below
It's worth remembering that Stewart's very silly joke was rooted in very real fears at the time. The 44th edition of the annual music awards show aired on CBS on Feb. 27, 2002, five months after the 9/11 terrorist attacks. The events of that day upended familiar air travel routines, leading to increased security measures at airports across America, many of which are still in place today.
The bit begins with Stewart walking onto the Grammy stage via an arched entrance that beeps after he passes through. "Step back through, please," requests a faux security officer — played by Jimmy Kimmel, who was one year away from launching his own late night show, Jimmy Kimmel Live. "I'm going to need you to empty your pockets and step back through." Stewart proceeds to offer up his cellphone, all the while expressing his ignorance about what could have triggered the alarm. "They already deloused me upstairs," he mock-protests.
The security officer then directs Stewart to remove his shoes — a reference to Richard Reid's arrest in December 2001 for hiding homemade explosives in his footwear. "Remember when people used to keep their drugs in there?" Stewart asks. "How's Willie Nelson ever going to get through?"
As the bit goes on, two hulking guards are brought onstage and proceed to roughly undress the comedian, until he's only standing in his skivvies. "He's alright," they eventually declare, and Stewart continues his emcee duties.
"Remember when security was tight because Eminem was going to sing with Elton John?" Stewart joked, referring to the previous year's awards when the controversial rapper and the legendary singer teamed up to perform Eminem's hit single, "Stan." "Those were the days, weren't they folks? 'They're going to duet — call the SWAT team!'" Stewart also shouted out the 2002 Destiny's Child anthem "Bootylicious" while music icons Tony Bennett looked on, laughing. "I don't think any of you are ready for this jelly, quite frankly."
Before shuffling offstage to get dressed, Stewart introduced the night's first presenters: Britney Spears and Matthew Perry, who kept the clothing-related humor going. "I was worried we'd be wearing the same outfit," Perry joked, gesturing to Spears's red dress. The Friends star then went on a super-cringey riff about how "right" it sounded for him to say "Britney and I" and how it suggested that "we belong together."
Spears gamely played along and let him down gently. "Matthew, this is kind of awkward to say in front of the entire planet and all, but I guess I kind of think of you as a friend," she said, putting extra emphasis on the "friend." To which Perry replied, "Yeah, I get that a lot," before reading off a list of nominees that included Backstreet Boys, Five for Fighting, NSync, R.E.M. and U2.
While none of those groups — those that are still around anyway — are up for awards at this year's Grammys, there is a shared connection between the 2002 and 2022 telecasts. Current Daily Show host, Trevor Noah, will host the awards for the second year in a row. And unlike Stewart, who currently anchors his own talk show on Apple TV+, he'll probably keep his shirt on.
The 2022 Grammy Awards will air Sunday, April 3 at 8 p.m. on CBS and Paramount+.