There is very little work to go around in Hollywood these days. So to stay inspired over the past several months, Emily Winter has met with a writing group on Zoom each weekday morning at 10 a.m.
Celeste, do you have a meeting? You look fancy.
Do you play softball? I can put you on the sub list!
What’s everyone working on today?
During one such meeting last spring, Winter remembered that she had tickets to an upcoming taping of “The Price Is Right,” where every audience member is eligible to win prizes like a billiards table or a car. “My hottest iron in the fire,” she explained to her writing group.
Then she took a beat to think.
She had used up all her unemployment. She was starting to panic about her dwindling savings account. And she did not have anything better to do. Why not figure out how to increase her chances of being selected to compete on the game show?
“Let’s win some $$$,” she wrote in an email to two friends when she invited them to attend the taping in May, “or a weird boat!!!!!”
Building a Career
For a long time, Winter felt that she was good only at writing. She tried journalism and got an internship with The Associated Press but thought covering terrorist attacks was depressing. While working for a local newspaper in Wisconsin, she found that reporting on fights over “what color the slides should be at the playground” was depressing in a different sort of way.
Winter turned to television writing at 22 and moved to New York after getting an internship with “The Colbert Report.” She met her writing partner there and piled up credits: an NPR radio program, shows on Fusion TV, E! and TV Land. A gig with Nickelodeon writing for “That Girl Lay Lay” nudged Winter and her husband to move to Los Angeles in 2022.
But in 2023, writers like her went on strike. Then the actors joined them. After the parties finally reached agreements, Winter’s Nickelodeon show was abruptly canceled. Studios, faced with higher labor and production costs, decided their streaming platforms needed to make money and began slashing the number of projects.
As has been the case for so many people whose labor powers Hollywood, Winter has struggled to find formal employment ever since. Pitches have been met with silence or polite passes. She and her writing partner were recruited for a show, only to be told they could not ultimately be squeezed into the writers’ room, she said. Members of her writing group have been getting turned down, too.
By May of this year, Winter estimated, she had drained her business and personal bank accounts to about $10,000. She would welcome a weird boat.
“There were just constant possibilities” when she first came to Los Angeles, she said. “Now, there’s nothing.”
Her husband, Chris Calogero, is an actor and comedian. His income from his other work, in the legal department for “Judy Justice,” the “Judge Judy” reality series, has not been enough to cover the couple’s expenses. Because Winter has had so few working hours logged, she eventually lost her union health insurance too.
If only there was a way to give herself a little cushion, she thought. Industry professionals had started throwing around the phrase “Survive till ’25.” But Winter had done the math and was becoming increasingly unsure if even that was possible. A few months ago, she examined her budget and determined that she could pay the rent only through November.
“I can’t make it another year if I don’t get a job,” she told herself.
‘A Drought of Jobs’
To keep her sanity and make some money between writing jobs, Winter, 40, has turned to softball and standup comedy. In addition to passing the time, the activities have helped her stay plugged into work circles while reinforcing that she is not alone. “Nobody’s working right now,” she said.
In New York, writers might commiserate inside a bar. But in Los Angeles, they do it outside. Winter is the captain of the Stutzmans, a softball team named after Ellen Stutzman, the chief negotiator for the Writers Guild of America during last year’s strike.
One weeknight last month, Winter was penciling in the batting order for her team’s title game. Though there was no cash prize, there was a trophy at stake. “I really want to win,” Winter said a few days before the game, which the Stutzmans did, in fact, win.
“It has been really, really important for her,” her husband said. “I think it’s helpful for her brain to understand this is no fault of your own, there’s a drought of jobs in the city. Other writers are also in the same boat.”
About a week later, Winter sat halfway up a staircase inside the Paramount, a music venue in the Boyle Heights neighborhood of Los Angeles. More than 100 comedians and audience members bustled around her. They were there for one of her events, “One-Liner Madness,” an N.C.A.A. Tournament-style competition in which 64 comedians deliver jokes until the crowd picks a winner.
Winter usually keeps the profits from ticket sales. But although she desperately needed the funds, she had made it a tradition at her Los Angeles show to donate the earnings to the local nonprofit that once was home to her dog.
“Proceeds from this show go to the Pitty Committee animal rescue,” she said to open the show. “If you happen to have money — so, not the comedians — and you want to donate more, there’s their Venmo on the table.”
“Here’s what else,” she added. “I am sad, I am poor.”
“If you would like to fix that,” she continued, “you can buy merch from Becca in the corner over there.”
Game Theory
In the weeks before she was scheduled to attend “The Price Is Right” in May, Winter began watching YouTube videos about the show. There was one on how producers choose contestants. (Be upbeat! Don’t say you work in show business.) Others explained how to win pricing games and bidding wars. (If the prize for the game Coming or Going is a trip, always guess the Going price.)
When the day of the show finally arrived, Winter lined up with her guests before the taping in the Atwater Village neighborhood of Los Angeles. Many of the audience members wore bright homemade shirts, hoping they would be deemed interesting enough to join the host, Drew Carey, on television. Winter and her friends wore hot pink button-up shirts featuring a pineapple-and-palm-tree print. Calogero opted for a colorful jumpsuit with palm fronds.
It took about an hour for Winter to get inside to a holding area. There, a producer quizzed her and a dozen other attendees, speed-dating style, as crew members surreptitiously took notes. When the producer got to Winter, she said she was a trivia host from Chicago. (Which was sort of true: She wrote a book on trivia.)
Winter rationalized that she had worked hard, so she allowed herself to hope she would be selected. A short time later, the cameras were on and the crowd was going crazy.
“From Hollywood, television’s most exciting hour, it’s ‘The Price is Right!’” the public-address announcer said.
“Emily Winter — come on down!”
Screams of Delight
Four months after the taping, Winter sent her friends a party invitation. It had a picture of Carey’s smiling face faded behind text that said, “You’re invited to a pizza party for absolutely no reason!”
There was certainly plenty of pizza at Winter’s apartment on Oct. 11: the “trashy” frozen kind, deep dish from the Chicago staple Gino’s East and artisan pies from Pizzana down the street. And there was, despite what the invitation said, a reason for a party: to watch her “Price Is Right” episode on the day it aired.
“So, this game is hackable,” she said as they watched a young contestant named Wyatt be presented with a trip to Saint Lucia. It was the game Coming or Going.
Then the camera was back on Winter, as a new set of bids began.
“Four-fifty.”
“Five hundred.”
“Eight hundred.”
“Emily?” Carey prompted.
“Eight-oh-one,” Winter said.
Actual retail price of the new hand-woven hammock?: $1,248.
Winter screamed on the television. Her friends screamed inside her Sherman Oaks apartment. One frantically pointed to the guest room, where several long, unopened boxes — almost certainly holding a hand-woven hammock — were being stored.
Her friends watched as Winter struggled with an exceedingly difficult and rarely played game that she had not encountered during her studies, missing out on a camping trailer.
“It’s like the hero’s journey,” said Chuck Kim, a member of her writing group. “She has to lose before she wins.”
A Weird Boat
All hope was not lost: Every contestant who makes it onstage gets a chance to compete for the grand prize, and Winter still had her turn at the big, heavy wheel.
After failing to spin it all the way around the first time — “the most embarrassing thing,” she said later — she spun and landed on 95 cents. As the closest contestant to $1, she moved on to the Showcase Showdown.
Her showcase would be what she later called a “Midwestern dad pack”: a patio set, a riding lawn mower and — wouldn’t you know it — a power boat.
She bid $23,500, well under the value of the prizes. But the other contestant’s bid was even further away from his showcase’s actual price.
Winter screamed on the television. Her friends screamed inside her apartment. “I needed this so bad,” she recalled telling a stranger as she left the CBS lot after the taping.
By about 9 p.m. on the night of her party, most of the pizza had been consumed. A cake featuring Winter’s face and the actual cost of the showcase, $32,730, waited to be sliced.
Winter stood up on her apartment’s staircase, slightly hidden from her friends’ view. There was important business to attend to.
“I’ve gathered you all here,” she said, “to see if you would like to buy a riding lawn mower.”
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