Manager-Producer Rory Rosegarten On Relishing The “Tough Fight” Of Today’s Hollywood, Connecting With Tom Green & Why ‘Everybody Loves Raymond’ Will Never Be Rebooted
The world of agents and managers is known for producing wunderkinds, phenoms barely out of school who ride rocket ships from the mailroom to the corner office and beyond.
Rory Rosegarten’s story got off to a similar kind of fast start, but it happened outside of the traditional corridors of Hollywood power. By the age of 20, he was repping comedian Robert Klein and starting to build a client roster, but his trajectory from there got more interesting than the Sammy Glick/Entourage clichés about talent representation. The two-time Emmy winner for Everybody Loves Raymond (Ray Romano is a 38-year client) has become an increasingly prolific producer. Three projects centered around Tom Green, another client, are landing this month on Amazon Prime Video.
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Rosegarten, 62, grew up on Long Island and is still running the company he founded in 1982 after meeting comedian Klein on a freelance interview assignment for Playboy. His solo management shingle, which he launched after dropping out of Arizona State after his sophomore year, is called The Conversation Company. A conversation with Rosegarten about his company makes it abundantly clear that the boutique was never fated to be a stepping stone on the way to running a studio or running a multi-national conglomerate.
“I only have 10 clients and I wanted to keep it low,” Rosegarten told Deadline. “There are management companies and managers who have many more clients, and I’m not criticizing how they work. But the way I work is I like to roll up my sleeves. When a lot of the managers who I started with joined larger concerns, I didn’t. I remained independent because I always felt very strongly about, if I make a decision and it’s wrong, I can sleep at night. But if you make a decision that’s wrong that affects me, I can’t sleep at night. I just wanted to be my own person because that worked better for me.”
Rosegarten has kept a low profile by the standards of Hollywood, though he finds himself more in the spotlight lately, in part because of Green’s unlikely trio of titles all debuting on Prime Video this month. The first, a documentary feature directed by Green himself, premieres tonight. The others, a stand-up special and a docuseries about his renovation of a 100-acre farm in Canada, will follow next week.
While Romano, Brian Regan and other clients have been with Rosegarten for decades, Green is a newer addition to the roster. The two connected during a visit to Israel just prior to Covid, and then had more time to discuss Green’s plans during the pandemic. Green, whose previous manager, Howard Lapides, died in 2019, eventually signed with Rosegarten.
Green, a chameleonic presence in popular culture over the past three-and-a-half decades, immediately seemed like a noteworthy additon to Rosegarten’s roster. He can be considered “the godfather of podcasting,” the producer says, and has often been ahead of the curve, anticipating the “broadcast yourself” ethos of YouTube. While Rosegarten smiles that it’s “weird to direct a documentary about yourself,” he says Green’s project benefited from a trove of archival footage.
“He’s been filming himself since he’s 16, maybe even longer than that,” Rosegarten says. “He not only tells you about all the things he’s done, you get to see him do them.”
After initially focusing only on projects directly involving clients, Rosegarten has started branching out as a producer. Among the projects he is attached to are a film set up at Netflix about punk rock band the Ramones and a series with Village Roadshow about golfer John Daly. The latter project is executive produced by comedian Gary Valentine, a Rosegarten client and frequent collaborator of Kevin James who wrote and acted in The King of Queens, longtime CBS primetime running mate with Everybody Loves Raymond. Rosegarten and Valentine have teamed to launch Valentine-Rosegarten Productions, which also has a sitcom in development for Adam Sandler’s Happy Madison.
Reflecting on his journey through show business, Rosegarten acknowledged that the process of making any project has changed dramatically from the pre-streaming heyday of overhead deals and sitcoms greenlit based on a comedian’s material. “It is a tough fight,” he said, in part because “as a manager, you have to be the biggest cheerleader and the severest critic all in one. Your clients have to trust you.”
As far as why he never wanted to leverage his company to grab a bigger brass ring, Rosegarten replied, “I like being a manager. It’s modern. I’m not old-school, but I am old-school. I like being a manager. I like the relationships and talking strategy, talking to the clients about ‘Should we make a left or make a right?'”
The mood of Hollywood has darkened in recent years, Rosegarten acknowledges, due to the dual strikes of 2023, the impact of Covid and wave after wave of cost-cutting.
“Show business is going through a very tough time right now with the streamers,” he said. “Change isn’t necessarily a bad thing, it’s just that. It’s change. … I like the change. It’s scary. There have been a lot of heavy changes and that is scary for a lot of people. But I think ultimately show business will find its way because it always has.”
All of the principals involved with Everybody Loves Raymond are often asked whether it will ever return in some form given the TV industry’s obsession with reboots. Rosegarten doesn’t mince words addressing the topic. “There will never be a reboot of Raymond,” he declares.
One big hurdle, Rosegarten notes, is the fact that original cast members Doris Roberts, Peter Boyle and Sawyer Sweeten have all died in recent years. Even if that could be accounted for by writers, though, “a reboot is never as good as the original,” he added. “It just isn’t, more times than not. Raymond captured lightning in a bottle for nine years, 210 episodes. They don’t want to touch it. It is exactly what it is. It would be like doing a reboot of The Honeymooners.”
Even a payday with a lot of zeroes attached to it wouldn’t change Rosegarten’s mind. “I’m very interested in the art of it, not the business of it,” he says. “I do what I do because I can’t do what Ray does. I don’t have that ability. This is as close as I’m going to get.”
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