After graduating, he stayed in London pursuing a career in acting, when he auditioned for and landed the role of Private John Zielinski in the HBO World War II epic, Band of Brothers.

[3] In New York, he was encouraged to take improvisational comedy classes at the Upright Citizens Brigade Theatre, where he began "advancing rapidly through the UCB hierarchy until Chris Gethard invited him to join his troupe, the Stepfathers."

For years, Ratliff had been "too ashamed to even tell the Hanks story", but at the UCB Theatre he "realized it was a good ice-breaker, in part because every actor has experienced professional rejection and disappointment."

He began by enlisting friends, such as Jon Hamm, D'Arcy Carden, Adam Conover, Bobby Moynihan, and Zach Woods, to tell and expand upon the Hanks story as well as share their own experiences with rejection.

[6] Initially, Ratliff was having a hard time finding a serious distributor for the show, though he was not deterred: "I was going to continue doing this podcast no matter what, but I wanted to do it well because I knew it was a good idea.

"[7] With producers Mike Comite and Harry Nelson working with Ratliff (as well as Jordan Allyn joining in season 3), Dead Eyes quickly found critical acclaim and a wide audience as Ratliff gained momentum through its first three seasons, holding interviews with Band of Brothers cast members Ron Livingston, Stephen McCole, and Adam Sims, the actor to whom the Zielinksi role was given.

[8] It was revealed that Colin and sister Elizabeth had made their father aware of Ratliff's story and podcast: upon learning of Dead Eyes, Hanks said, "I was aghast.

[10] The 90-minute interview between Ratliff and Hanks was hailed as a momentous achievement in podcasting, a "rare show that gives you a perfect conclusion",[11] "surprisingly funny and empathetic",[12] and an event Paul Scheer called "thrilling".

"[16] Other times, Ratliff would record field audio on his phone from various locations, such as a busy street corner in New York City, and send the footage to Comite and Nelson.

[19] For Vulture's "Best Podcasts of 2020", Nicholas Quah said: "Fascinating and excellent... Part interview show, part memoir, Dead Eyes is an innovative take on a familiar genre",[20] and on The New Yorker's "Best Podcasts of 2020", Sarah Larson wrote: "In probing themes of opportunity, rejection, and turning failure into art, Ratliff and his guests (including Jon Hamm, Rian Johnson, and Aimee Mann) manage a level of entertainment and tonal nuance that is, frankly, surprising.

"[21] For IndieWire's "Best Podcasts of 2020", Steve Greene wrote: "Ratliff takes a self-aware search for a likely impossible answer and uses it to show how hard it can be to cope with rejection.

"[22] Esquire's Emma Carey says: "Ratliff explores not just the ups and downs of show business, but the more deeply human experience of dealing with personal and professional failure.

"[25] and Nicolas Quah from Vulture says "The themes Dead Eyes persistently explores are rich and endless, and its tenor captures the feeling of navigating life’s greatest anxieties.