Air date: May 6, 1960
Gart Williams (James Daly) works for an advertising agency, a job which he is ill-suited for. After his young protege fails to show up for an important business meeting, sending a telegram that he'll be working elsewhere (and taking a $3 million automobile deal with him), Gart is reprimanded by his boss. He's quick to snap back, but instantly regrets it. On a train ride back home, he dreams of arriving at a place called Willoughby, a small town stuck at summer in 1888. Before he can properly explore the place, he awakens back on the train.
Back home, Gart gets into an argument with his wife Janie, who's fed up with how sensitive and emotional he is. Gart hasn't lost his job, since he's still tied to a few deals that his boss would hate to lose, but he is tired of the masquerade he must pull off every day to succeed in the world. He realizes that he'd truly be much happier in a place like Willoughby, though Janie derides him for wanting to give up a profitable job to become "Huckleberry Finn". The next time Gart rides the train, he's told that there's no such place as Willoughby by the conductor, but still dreams of it again. He once again awakens before he can explore it, however, and vows to actually enter Willoughby the next time.
Gart's next day at work is horrible; he has a breakdown due to stress, and when he attempts to call his wife for reassurance, she is of no help at all. On his very next train ride, he again dreams of Willoughby, and purposely abandons his briefcase in order to leave at the station before the train departs. He's immediately welcomed by the townsfolk, and he walks into town as an elderly conductor checks the clock...which immediately transitions to a younger conductor's lantern. He and the rest of the train staff are discussing the fate of Gart Williams, who from their perspective, leapt from the train while shouting about Willoughby and died the moment he hit the ground. His corpse is carried into a hearse, and on its back door is written the following: Willoughby & Son Funeral Home.
A Trope at Willoughby:
- Born in the Wrong Century: Gart's wife Janie even invokes the trope, saying he was born too late. Gart agrees.
- Broken Record:Misrell: This is a push business, Williams. A push-push-push business. Push and drive! But personally, you don't delegate responsibilities to little boys. You should know it better than anyone else. A push-push-push business, Williams. It's push-push-push, all the way, all the time! It's push-push-push, all the way, all the time, right on down the line!
- Big "SHUT UP!": "Fat boy, why don't you shut your mouth!"
- Bittersweet Ending: Implied. Gart has died in the real world but it's possible that Willoughby is an alternate dimension he's alive and well in.
- Driven to Suicide: Gart jumps off a train in motion, killing himself on impact. However, the episode's moments from his perspective indicate he saw himself as getting off safely and into Willoughby—and since this is The Twilight Zone, maybe he really did.Gart: Willoughy. Next time, I'm going to get off!
- Fat Bastard: Mr. Misrell. Lampshaded by Gart.
- Foreshadowing: At the very beginning, after Gart angers his boss, his secretary asks if he'd like anything. She's asked for a razor and a diagram of the human circulatory system, showing that Gart's no stranger to suicidal thoughts...
- Gainax Ending: Is the ending a happy or sad one?
- The Gay '90s: Technically, a couple of years earlier. The conductor at Willoughby tells Gart it's 1888. But otherwise it fits all the aesthetics.
- Happy Place: Willoughby is an idealized escapist fantasy for Gart, however, another interpretation is that it is a type of Heaven at the end, given that he dies.
- Hen Pecked Husband: Aside from work, Gart is worn from trying to please his wife Janie and satisfy her "appetites". It's even implied that the reason he chose a career path he clearly didn't like in the first place was because she urged him to.
- Ironic Echo: Willoughby, the name of Gart's idyllic town that can't be found on a map, is actually the name of the funeral home which takes his corpse.
- Jerkass Has a Point: Mr. Misrell rubs it in Gart's nose that the new employee Jake Ross was not only too young for the company's project, but too unreliable and untrustworthy for it.
- Longing for Fictionland: Gart keeps dreaming of Willoughby, an idyllic 1880s town straight out of Mark Twain's work.
- Mean Boss: Or Bad Boss. Mr. Misrell may have a point that Gart is way too trusting with new employees, but his Broken Record of "push, push, push! Push and drive!" would make anyone go insane with annoyance.
- Meaningful Name: Mr. Misrell's name sounds like "Miserable", a very appropriate name for one who is head of a company that Gart is unhappy to work at.
- Nostalgia Filter: Gart's imagining of the 19th Century is a bit too idyllic.
- Rage Against the Reflection: Gart smashes the mirror in his office bathroom.
- Reality Ensues: Exactly what happens when you trust someone with a project without any wondering if they're dependable or even loyal to the company. Gart learns this the hard way in the prologue.
- Rich Bitch: Gart's wife Janie is a passive variation. She's cold, nearly emotionless, and is clearly using Gart's career to further their own social standings. It's apparent she doesn't care that his career path is making him stressed and miserable, and belittles his wish to live the simpler life. The next morning, when he has a breakdown and expresses how badly he wants to quit his job, it's strongly implied she leaves Gart when he needed emotional support the most.
- Rule of Three: It's the third time that Gart dreams of Willoughby that he actually departs the train.
- Snow Means Death: Whenever Gart's shown on the train, and at the end when we see his corpse, it's during a November snowstorm.
- Suspiciously Apropos Music: The final music the band plays in Willoughby is "Beautiful Dreamer". Subverted in that he's not "dreaming", per se.
- Take That!: Against The '50s ideals, which was something Serling himself wasn't a fan of.
- Tuckerization: Gart's advertising company is handling the Bradbury account. This is a reference to Ray Bradbury, who later wrote "I Sing the Body Electric".
- Ungrateful Bastard: Jake Ross, the new employee that Gart gave the new project to. Gart wholeheartedly entrusted he would help the company with this project, and instead, he stabs him in the back and takes the project to another company, leaving poor Gart high and dry.
- Wham Shot: The final shot of the Willoughby hearse.