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Inside Ari Emanuel’s Grueling First Job in Hollywood’s Powerful CAA Mailroom

His journey to the top began with thankless assignments, angry executives and nights spent sleeping on couches.

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Inside Ari Emanuel’s Grueling First Job in Hollywood’s Powerful CAA Mailroom

Long before he negotiated billion-dollar deals, represented some of entertainment’s biggest stars and helped build a global business empire, Ari Emanuel was completing coffee runs and making sure another man’s bathroom had enough toilet paper.

That man happened to be Michael Ovitz, the legendary co-founder of Creative Artists Agency who was once considered the most powerful talent agent in Hollywood.

In an excerpt from his new memoir, Roll the Calls, Emanuel revisits his earliest days in Los Angeles—when he had little money, no permanent place to live and only a distant view of the influence he would eventually command.

The result is an unvarnished picture of old Hollywood’s mailroom system: exhausting hours, rigid hierarchies, relentless criticism and young employees competing for the smallest opportunity to prove themselves.

Arriving in Hollywood with nowhere permanent to stay

After graduating from Macalester College in 1983, Emanuel briefly pursued professional racquetball and worked for New York talent agent Robert Lantz.

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His ambitions, however, were fixed on Hollywood.

Emanuel became fascinated by Ovitz, whose reputation had transformed CAA into one of the entertainment industry’s most feared and influential agencies. In 1987, he moved to Los Angeles and joined the company as a trainee.

The move was far from glamorous. According to his memoir, Emanuel initially relied on friends and acquaintances for places to sleep, moving between couches while attempting to establish himself in an unfamiliar city.

There were no celebrity dinners, private aircraft or multimillion-dollar contracts waiting for him. His daily reality involved sorting mail, collecting coffee, running errands and responding instantly to the demands of senior agents.

Yet even the most ordinary tasks carried enormous weight. A late delivery or incorrectly prepared drink could become a public lesson in failure.

The CAA mailroom was Hollywood’s unofficial boot camp

The mailroom at CAA was not simply an administrative department. It functioned as an intense training programme and a testing ground for aspiring agents.

Young employees were expected to learn the names, habits and preferences of powerful executives and clients. They delivered scripts, answered telephones, organised paperwork and studied the business whenever a spare moment appeared.

Emanuel’s responsibilities reportedly extended to checking Ovitz’s private bathroom and replacing its toilet paper. It was the kind of assignment designed to reinforce the distance between those at the bottom of the agency and those already sitting at its summit.

For ambitious trainees, however, humiliation was part of the bargain. The mailroom offered access to a business that was otherwise nearly impossible to enter. Those who survived could become assistants, and assistants might eventually earn the right to represent clients of their own.

Emanuel ultimately rose from trainee to mailroom chief and then became an agent’s assistant. Reading scripts remained difficult because of his dyslexia, but he took material home at night and forced himself to keep learning.

A culture powered by shouting and fear

Emanuel’s account also explores a workplace culture in which yelling was treated almost as a management technique.

“Sometimes it feels as if the yeller is actually getting off,” he writes, before suggesting that some senior employees were simply repeating the treatment they had received during their own mailroom years.

The observation captures a cycle familiar to many competitive workplaces: one generation suffers under an unforgiving system, rises through it and then subjects the next generation to the same behaviour.

Emanuel does not present himself as entirely separate from that culture. His own temper later became one of his defining characteristics, earning him a reputation as an exceptionally forceful—and frequently confrontational—negotiator.

That personality also helped inspire Ari Gold, the explosive fictional talent agent played by Jeremy Piven in HBO’s Entourage.

In Roll the Calls, Emanuel examines rage not simply as a personal flaw but as a source of energy that helped him survive rejection, professional insecurity and the pressure to prove himself.

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His departure from CAA was equally explosive

Emanuel spent approximately two years at CAA before former colleagues invited him to join the newly established InterTalent.

When he informed Ovitz that he intended to leave, the conversation allegedly became heated. Emanuel has previously claimed that Ovitz threatened to destroy the careers of those involved, prompting him to pick up a chair and demand to know whether he was being threatened.

Ovitz has disputed Emanuel’s account of the confrontation.

Looking back, Emanuel has acknowledged that challenging one of the industry’s most powerful figures in such a manner was reckless. But the episode also illustrates the stubbornness that would repeatedly shape his career.

He later worked at International Creative Management before co-founding Endeavor in 1995. The agency eventually merged with the historic William Morris Agency, creating one of Hollywood’s dominant representation businesses.

From delivering coffee to reshaping global entertainment

Emanuel’s career eventually expanded far beyond traditional talent representation.

He helped lead Endeavor’s acquisition of the Ultimate Fighting Championship in a deal valued at more than $4 billion. UFC was later combined with WWE under TKO Group Holdings, turning Emanuel into an influential figure across entertainment and professional sports.

His client relationships have included celebrated figures such as Oprah Winfrey, Martin Scorsese, Larry David and Mark Wahlberg.

Roll the Calls, written with Pulitzer Prize-winning author J. R. Moehringer, does not simply celebrate that ascent. It examines Emanuel’s dyslexia, volatile personality, professional feuds, family relationships and the personal cost of pursuing power with relentless intensity.

The audiobook is narrated by Bob Odenkirk, one of the significant early clients in Emanuel’s career. The memoir was published by Alfred A. Knopf on September 22.

The most revealing part of Emanuel’s story may not be the fortune or influence he eventually accumulated. It is the distance between the man who now commands boardrooms and the young employee who once slept on other people’s couches, carried coffee through office corridors and quietly replaced his boss’s toilet paper.

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Taylor Swift won Video of the Year at the 2026 VMAs. So how did Madonna leave with seven trophies?

Swift claimed the night’s top video prize, while Madonna led all winners at the Snoop Dogg-hosted ceremony in Los Angeles.

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Taylor Swift won Video of the Year at the 2026 MTV VMAs, while Madonna led the night with seven awards.

The biggest prize went to Taylor Swift, but the biggest haul belonged to Madonna. At the 2026 MTV Video Music Awards, Swift won Video of the Year for “The Fate of Ophelia,” while Madonna finished the night with seven awards.

The ceremony took place on Sunday, September 27, at the Peacock Theater in Los Angeles, with Snoop Dogg as host. Madonna collected three of her awards during the televised show: Artist of the Year, Best Dance for “Confessions II – The Film,” and Best Collaboration for “Bring Your Love” with Sabrina Carpenter.

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Swift took the top video prize

Swift’s Video of the Year win was only part of her night. She also won Best Direction for “Opalite” and received the inaugural Artist Director Honors, recognising her work behind the camera. The honours added another chapter to a VMA career that has increasingly celebrated her as both a performer and a director.

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Madonna’s wins reached across performance and filmmaking. Alongside her three televised awards, “Confessions II – The Film” won Best Cinematography, Best Choreography and Best Long Form Video. Her album Confessions II took Best Album, bringing her total to seven. She also returned to the VMA stage as a performer for the first time in 23 years.

There were other names to celebrate. BTS won Song of the Year for “Swim,” Best K-Pop for “SWIM” and Best Group. Sienna Spiro was named Best New Artist, while LISA won Best Pop for “Dream” featuring Kentaro Sakaguchi.

For Swift, it was a night crowned by the award every Video of the Year nominee wanted. For Madonna, it was a sweeping return to the VMA spotlight: seven trophies and a performance that brought her back to the show’s stage after more than two decades.

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Chuck Lorre’s Award Night Began With Charity and Ended in Political Debate

Recognized for supporting meals for people facing serious illness, he used his speech to address Trump and the Democrats.

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Chuck Lorre’s Award Night Began With Charity and Ended in Political Debate

Chuck Lorre was meant to be accepting an award for his philanthropy. He used the microphone for something considerably less conventional: a speech that took swipes at Donald Trump, Melania Trump, the political left and Robert F. Kennedy Jr..

The television producer spoke on Saturday, September 26, at Project Angel Food’s Angel Awards in Los Angeles. His daughter, director Nikki Lorre, presented him with the Founders Angel Award, the organisation’s highest honour and one it has given only once before in its 37-year history.

Lorre began by acknowledging the pressure on a comedy writer to get laughs. Then he turned to politics. He said he wanted a government more concerned with people’s health and welfare, before launching into a profane joke about President Trump. He also made a harsh personal remark about the first lady, contrasting her with Michelle Obama. The comments were part of Lorre’s routine, rather than claims established by the event.

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His criticism did not stop with Republicans

Lorre urged the Democratic National Committee to move away from what he called “far-left woke culture” and seek a “common sense middle ground” with working-class voters. He quickly turned that point into another joke, this time targeting Kennedy over vaccination. His remarks moved between political argument and punchline, with little interest in the polite script of an awards acceptance speech.

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The setting gave the speech another dimension. Project Angel Food prepares and delivers medically tailored meals for people facing serious illnesses in Los Angeles County. Lorre’s family foundation helped make its expanded kitchen and campus possible; according to the organisation, the project increased its annual meal-production capacity from 1.5 million to more than 4.5 million. The gala raised more than $1 million, according to the event coverage.

Lorre may have delivered the night’s most provocative lines, but the award recognised work with a practical effect: helping the charity put more meals in the hands of people who need them.

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‘Avatar’ Overtaken: ‘Avengers: Endgame’ Is Back on Top

Marvel’s return to the big screen reshapes the race for the highest-grossing film of all time.

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‘Avatar’ Overtaken: ‘Avengers: Endgame’ Is Back on Top

Seven years after its original release, Avengers: Endgame has unfinished business at the box office.

The Marvel Studios blockbuster has overtaken James Cameron’s Avatar to become the highest-grossing film worldwide once again. According to The Walt Disney Company’s October 4 announcement, Endgame now holds an estimated $2.9255 billion, narrowly ahead of Avatar’s $2.9237 billion. That puts just $1.8 million between two of cinema’s biggest hits.

The lead is small. The comeback, however, is substantial: a film released in 2019 has drawn enough fresh ticket sales to rewrite the all-time chart.

The ‘Encore’ release that tipped the balance

The latest theatrical run, titled Avengers Endgame: Encore, has earned $126 million worldwide, according to TheWrap. That includes $36.2 million in North America and $89.8 million from international markets—the extra business that pushed the film back into first place.

Audiences also had a reason to return beyond revisiting a familiar blockbuster. TheWrap reports that the reissue features a modified ending and three new scenes during and after the credits, connected to Avengers: Doomsday. The release therefore serves two purposes: bringing an established favourite back to cinemas and giving viewers a bridge to the next Avengers story.

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A rivalry with a history of reversals

This is another change of leadership in a box office contest that has lasted for years.

Endgame first displaced Avatar in 2019. Cameron’s science-fiction epic regained the crown following its Chinese re-release in 2021. Now, another theatrical return has swung the result in Marvel’s favour. Re-releases have become a decisive part of the competition, extending both films’ earning lives well beyond their original runs.

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The distinction matters: this is the record for worldwide theatrical revenue without adjustment for inflation, including re-release earnings. It measures money collected rather than the number of tickets sold.

Why ‘Endgame’ matters to ‘Doomsday’

The timing gives Marvel’s comeback an added significance. Avengers: Doomsday is scheduled to reach cinemas on December 18, 2026, and Disney has positioned Endgame as an important foundation for that next chapter.

Explaining the connection, Anthony Russo said: “You really need to pick the story up from where you left it in Endgame.”

That makes this return more than a victory lap. A film remembered for closing a major chapter of Marvel’s story is now helping introduce the next one—and, along the way, has taken back Hollywood’s most closely watched box office title.

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