the (UN)LUCK IEST guy from mid-missouri

After decades of failures, CONNOR RATLIFF is finally having his moment — thanks to his unrelenting persistence, one-of-a-kind sense of humor and, most importantly, his dead eyes.

STORY BY AUSTIN WOODS

EDITING BY EMMA LINGO

Before landing roles on television shows like The Marvelous Mrs. Maisel, before the success of his Dead Eyes podcast and before touring with the Upright Citizens Brigade, Connor Ratliff was a 17-year-old from Jefferson City set on attending MU — he was so sure of it that he didn’t even bother applying anywhere else.

Everything about the university enticed Ratliff. It wasn’t far from his hometown, he was promised a theater scholarship and he had just finished starring in the MU Theatre Department’s production of Ordinary People alongside a college-aged cast (including future Mad Men lead actor Jon Hamm). The experience left a considerable impression on him, cementing his plans to enroll and pursue a theater degree.

But his time at MU was short. After two years, it became clear he wasn’t a good fit for the university. He was cast in few plays, despite auditioning for every single one, and his drama classes weren’t much help, either. The feedback he received from professors wasn’t useful — at worst, their comments only made him self-conscious about his style of acting. “Your way of acting is more about what you’re concealing than what you’re revealing, and that’s not really the best way to do it,” Ratliff recalls one instructor telling him. Although he transferred to the Liverpool Institute for Performing Arts (LIPA) in London, Ratliff has never regretted his time at MU. “Sometimes you learn what you’re supposed to learn in class, and sometimes the more important things you learn are from things that go wrong or just happen to you,” he says. “You have to be on the lookout for those, so when you have a bad experience it’s not just a bad experience. You want to be able to try and learn from it.”

Ratliff has had plenty of bad experiences to learn from. Throughout his career, he has experienced countless failures — failed auditions, failed projects — culminating in his firing from the HBO miniseries Band of Brothers by the most likable guy in Hollywood, Tom Hanks. This incident inspired the creation of his acclaimed podcast, Dead Eyes, which focuses on moments of personal and professional rejection.

Life is no movie; we’re not afforded the benefit of a neat three-act structure or a pleasant resolution like our favorite characters from the screen and the stage. Instead, our journeys are nonlinear, filled with dips, peaks, stops, starts and, above all, failure after failure after failure.

The folks in the entertainment industry know this all too well. Every actor is familiar with the acute sting of rejection, and some have even turned those losses into strengths. But few have done this to better effect than Ratliff.

Growing Up In Missouri

Even as a child growing up in Jefferson City, Ratliff knew how to use a negative experience to his advantage. When he couldn’t land a part in a community theater production, he and his friends would simply put on plays of their own at a nearby park. It didn’t stop there — grocery stores, office buildings and apartment rooftops became film sets where the group made movies with a cheap camcorder. “That’s continued into my current career,” he says. “It’s way too limiting to just wait for the roles and the job offers to come along. I’m too impatient for that.”

Ratliff grew up in a creative family. His mom, Greta, was involved in a community theater in Jefferson City, and his dad, Bill, was a weatherperson for KRCG as well as the host of a local children’s television show called Showtime Ratliff’s first on-screen interview was on his dad’s show, where he discussed his role in a local production of Oliver! and the intricacies of Porky Pig cartoons.

He didn’t know it at the time, but his eventual failure and firing by Hanks was foreshadowed as early as his freshman year at Jefferson City High School. In episode 30 of Dead Eyes, Ratliff details how he was cast for a small speaking role in the school’s 1990 production of South Pacific, even though he desperately wanted to play the show’s comedic leading character, Luther Billis.

Years later, Ratliff learned of another production of South Pacific from 1974 at Skyline High School in Oakland, California. At this show, the role of Luther Billis was played by none other than Hanks.

Ratliff’s role in MU’s 1992 production of Ordinary People at age 17 was his first serious gig, inspiring him to enroll in the university the following year. When his sense of belonging at MU waned, he once again decided to take a bad experience and make it good, booking a plane ticket to New York to audition for LIPA, where he was later accepted.

LIPA prides itself on its industry connections. Ratliff attended knowing the school was committed to securing agents and acting work for its students after graduation. And for him, that’s exactly what happened.

“I got an agent right out of drama school, and within months of graduating I was living in London (and) I was performing a lead role at the Royal Court Theatre on the West End,” he says. “I was thinking, ‘Well, now I’m a professional actor, for real.’ I imagined all of this was going to go really well for me.”

But the specter of failure soon crept up on Ratliff once again, as he found it increasingly difficult to secure parts after his stint at the Royal Court Theatre ended. He remained in London, taking a job at Ticketmaster in Leicester Square and kept auditioning for roles, most of which he didn’t even want in the first place. “I don’t think I booked anything in the year 1999,” he says.

The Breaking Point

In 2000, as the rest of the world looked forward to a new millennium, Ratliff’s acting prospects started to improve in London. Production for Hanks’ and Steven Spielberg’s Band of Brothers was in full swing, and he earned a small part in its fifth episode, directed by Hanks, who had just wrapped filming on Castaway

Ratliff was elated. This was his big break — the rising action in the overarching plot structure of his life — sure to result in more work and maybe even household-name status. After nearly a decade of ups and downs, Ratliff was finally about to be rewarded for his efforts.

Then he got the phone call.

His agent’s assistant was on the other end, panicking, frantically delivering the news that Hanks saw the audition tape and wanted to recast the part. Ratliff, Hanks felt, had “dead eyes.”

Dead. Eyes. For an actor, this might as well be a death sentence, and hear- ing it from Hanks — America’s Dad and Woody from Toy Story — was even worse. It was a knife plunged into a festering wound, a cruel, cosmic joke, a visceral reminder that disappointment is constant and nothing ever gets better. “I had this specific kind of failure, because it happened to feature a beloved Oscar-winning movie star,” Ratliff says. “At the time, it made a bad thing feel worse.”

In 2002, he moved to New York to look for a new agent and hopefully get his career back on track. With no luck, he quit acting entirely and began working at a bookstore in lower Manhattan the following year. “I didn’t even think about (acting),” he says. “I totally gave up on the idea that I was going to be an actor,” he adds. “I found that I was less miserable (at the bookstore) than I would have been if I was going out on auditions all the time.” But Ratliff’s passion was reignited after taking improv classes in 2009 at the prestigious Upright Citizens Brigade Theatre founded by Amy Poehler and Adam McKay. Five years later, he toured with the Upright Citizens Brigade and even performed at The Shack in MU’s

Student Center. Even though he doesn’t remember the details of this performance (he says improv shows are usually wiped from his memory as soon as they’re over), he recalls a positive reception from the audience and now hopes to perform in Columbia again sometime in the future.

A lot can go wrong during an improv show if your scene partner steers things in a direction you might not like, forcing you to compromise and work toward a scenario in which you can both thrive, entirely on the spot. This environment helped Ratliff grow as an actor and a person, teaching him how to adapt in the face of uncertainty. It was a major influence on the creation of his podcast.

“I don’t think I would have made Dead Eyes without that spirit of, ‘Well, what do I have, and what can I do with it?’” he says.

By 2015, Ratliff was signed to Forte Artist Management with agent Aaron Sandler. Sandler saw Ratliff performing at the Upright Citizens Brigade Theatre that fall as a detective in an improvised murder mystery show, and was immediately smitten by his candid style. Sandler says this personable approach distinguishes Ratliff from his peers and has carried over into his podcast.

“He’s very honest about his experience with being in this business, and that connects people to him on a very personal level,” Sandler says. “Especially on Dead Eyes, where he’s really baring his soul. It allows people to embrace their own insecurities. He takes it with a grain of salt and laughs at the absurdity of the business.”

Although Ratliff enjoys acting out other artists’ scripts, one of the reasons he is drawn to improv is the desire to write his own work. “I have that impulse to come up with stuff and devise my own material,” he says.

6 From Plays To Podcast

As Ratliff continued performing around New York, he quickly realized the “dead eyes” incident made for a good icebreaker — a quick, fun way of telling people who he was and how he wound up at Upright Citizens Brigade. Around this time, he frequently listened to true crime podcasts, such as Serial, in which a mystery was unpacked over the course of several episodes. This provided the impetus for his own podcast.

On the surface, Dead Eyes follows Ratliff as he investigates the reasons behind his firing from Band of Brothers But many episodes veer from this topic, and in the episodes that do focus on the mystery at hand, very little progress is made. This was a deliberate choice, as Ratliff wanted to approach the firing as a springboard for broader discussions about the nature of success and failure.

Since starting the podcast in 2019, Ratliff has brought on numerous bigname guests to discuss their own failures, including Seth Rogen, Judd Apatow and former Ordinary People co-star and fellow Missourian, Jon Hamm. In 2022, Hanks himself even made an appearance on the show, discussing the incident that gave the podcast its name, as well as his own tales of rejection.

Ratliff invokes his mid-Missouri background frequently on the show, and during the height of the COVID-19 pandemic, he recorded a string of episodes at his parents’ house in Jefferson City.

During one of these episodes (the eighth episode of the show overall), Ratliff interviews his parents, discusses a show business job he had recently lost and confides about his lockdown-era malaise. “We thought (the firing from Band of Brothers) was such a big deal at the time, and really, it wasn’t life or death,” his mother says in the episode. “The worst times in your life do pass. For most people, it gets better.”

Ratliff stayed with his parents for a total of seven months and recorded episodes of Dead Eyes in a blanket fort turned recording studio. “I would lie down on my stomach and Zoom with Seth Rogen from my parents’ TV room,” he says. “It was very strange.”

Ratliff has drawn from his Missouri background in other creative ventures as well. In 2012, he put on a one-man show at the Upright Citizens Brigade Theatre in New York called Local Authors Night at the Mid-Missouri Public Library Ratliff played all four roles — a worker at a small library in mid-Missouri and three local authors who were there to discuss their books. One of these authors was a boorish, profane yokel who, after being kicked out of the library’s book club, wrote a book of his own so he could be allowed back.

Ratliff spent close to a year writing and developing the project, and though the Upright Citizens Brigade directors decided not to continue with it, he considers it a creative success. “It would be one thing if it bombed, but it went really well, so I felt disappointed but also relieved,” he says.

Ratliff is currently working on podcast content and was cast in Paramount Pictures’ new Mean Girls movie musical playing teacher Mr. Rapp. A documentary crew is creating a film about his Upright Citizens Brigade-born cult comedy show, The George Lucas Talk Show. Ratliff hosts in the role of the famously uncharismatic George Lucas and invites famous guests to play along. Even at this unprecedented level of professional success, he remains aware of the constant possibility of failure. But now, he knows how to cope when the time comes.

“I always try to take a moment when things don’t go right to look it over and think, ‘What can I salvage from this?’” he says. “Don’t waste too much time sorting through the rubble, but see if there’s something you can take with you.”

Ratliff has salvaged more from his personal and professional failures than most people.