5 Ways of Seeing Gary from Chicago and the Tour Bus That Crashed the Oscars in a Jimmy Kimmel Prank

If the last-minute twist at the Oscars was seen to echo all the last-minute twists in American culture lately—the Super Bowl, the election—a silly five-minute segment earlier in the night should be noted for what it captured about the country’s ongoing tensions and tastes in iPhone peripherals.

Host Jimmy Kimmel’s team arranged for a sightseeing bus of supposedly “real” tourists to walk into the room, expecting a museum exhibit about the Oscars but instead finding themselves in the middle of the actual thing. “Welcome to the Dolby Theater,” Kimmel announced. “This is the home of the Academy Awards, which are, in fact, happening right now.”

The bit was both amusing and squirmy: a weird microcosm of Hollywood’s relationship with America, America’s relationship with the media, and Jimmy Kimmel’s ability to make everything a little more awkward than it needs to be.

The Hunger for Folk Heroes (and Memes)

At the front of the pack was the man who would be the moment’s breakout star, “Gary from Chicago.” In a room of tuxes, he wore basketball shorts, a baseball cap, and a “Hollywood” sweatshirt, with the gender-progressive touches of a purple phone case and a bag that might have been his fiancee’s purse. If the glitz ambush intimidated him, he showed no signs of it, happily introducing himself to stars and snappily replying to Kimmel’s jokes. On social media, pop culture’s craving for quirky symbolic everymen—see: Ken Bone, Joe the Plumber—quickly made itself known. So did the cravings of various corporate marketing teams.

Our Collective Phone Addiction

The dozen or so tourists seemed to realize what was happening at different rates, and with different emotions—fear, elation, nonchalance—but were united in keeping their phones in front of their faces. “You know we’re on TV so you don’t need to do that,” Kimmel said as Gary kept filming the room. His reply: “I know but I want to. I want to.”

The phone accessories themselves could make for a post-show fashion column: one woman had a sparkling jeweled case, another wielded a selfie stick as if it were a talisman. Devices in hand, the group pulled celebs in for selfies; Gary even handed his phone to Mahershala Ali as he posed with the actor’s Oscar.

For the tourists, it was a rare chance to see in the flesh people normally only ever seen on a screen. Yet they still insisted on having a screen between them.

Piercing the Hollywood Bubble …

In an era when Americans have become sharply aware of how isolated its various niches are—politically, socially, geographically—workaday citizens from around the country were literally bussed in for cultural exchange with the cultural elite. The stars received them warmly: Ryan Gosling offered up some sort of present to Gary, Jennifer Anniston handed over her sunglasses, Meryl and Mahershala and others grinned and hugged. Denzel Washington even “married” Gary and his fiancee Vicky, though it must be said this particular cinematic icon seemed in a bit of a hurry to return to his seat.

… or Reinforcing It

Oscars (Host) So White

The tourists were a mix of white and black and brown men and women. But Kimmel made the diversity seem anything but normal by using tired humor about “funny” names—which is to say, names unusual to white Americans. As the tourists entered the room, he had the crowd shout out “MAHERSHALA!,” the name of Moonlight’s Best Supporting Actor winner. Later, Kimmel reacted with horror when a woman of Asian descent told Kimmel her name rhymed with “jewelry.” When her husband said his name was Patrick, Kimmel replied with mock relief, “See, that’s a name.”

At an event that has recently been accused of white supremacy, this was a pretty tone-deaf shtick. But Gary, of course, helped deflate it. “I feel like you’re ignoring the white celebrities,” Kimmel said. Gary: “Because I am, though!”

The Insanity of Live TV

My stress reflexes were in full effect watching the segment, and judging from the cringing reactions on Twitter, I wasn’t alone. It’s definitely possible the tourists were just actors, or that they’d at least been coached to a greater extent than we were led to believe. But still, the spectacle of chaos in a space as highly choreographed, as widely watched, and as culturally fraught as the Oscars was riveting. At the very end of the night, viewers would be reminded of what makes live TV like this so electrifying—the potential for disaster, and miracles.