On their return home to the farmhouse, before Sullivan slips the bolt across the door of his upstairs bedroom for the night - for protection - an overly-attentive Miz Zeffie fusses over him and forces her way into his room to open his bed while singing: "Men must work and women must weep, or however it goes."

The portrait of Joseph changes his facial expressions in reaction to Sullivan's predicament. From the outside of Sullivan's bedroom door, Miz Zeffie turns the key and takes it with her to assure his stay. At the strike of "One" on the clock, Sullivan dresses in his hobo clothing and finds that he is trapped in a locked room. He crosses through the bathroom and opens the far door - but there lies Miz Zeffie fluttering her eyelids in the romantic light of her boudoir and asking: "Who is it?" He hastily closes the door and escapes from the room (and from the confines of the two sisters) through a second-story window and knotted sheets. In another slapstick scene, his pants are caught on a protruding nail. After ripping his pants, he lets go and drops into a rain barrel filled with water - a baptism into reality. He falls over and crashes into garbage cans before disappearing into the darkness. Now cold and shivering to death, he hitches a ride in a motor truck, explaining to the driver what he fell into: "Everything there was."

When he is shaken from a deep sleep the next morning, he finds that the truck driver has inadvertently taken him back to Hollywood: "You'll get a chance to meet the moon-pitcher stars - well, so long."

While buying a cup of coffee and doughnut in an all-night, roadside diner (an "owl wagon") with his meager ten cents, he meets a job-seeking, would-be, disenchanted and nameless starlet, The Girl (Veronica Lake) who is dressed in an evening dress (with a coat over it) and buying cigarettes at a machine. The failed, tough-talking, beautiful blonde girl is heading home after a disappointing time in Hollywood during tough times, but she takes pity on him and generously buys him a 35 cents ham and eggs breakfast even though she's broke. Although she has decided to give up on her ambitions to be a star, she matches wits with him, in one of the film's classic scenes:

Sullivan: You been in Hollywood long?
The Girl: Long enough.
Sullivan: Trying to crash the movies or something?
The Girl: Something like that.
Sullivan: I guess that's pretty hard to do, huh?
The Girl: I guess so. I never got close enough to find out.
Sullivan: Oh, sorry.
The Girl: Say, who's being sorry for who? Am I buying you the eggs or are you buying me the eggs?
Sullivan: Just like to repay you for them.
The Girl: All right. Give me a letter of introduction to Lubitsch. [A famous film director.]
Sullivan: I might be able to do that, too. Who's Lubitsch?
The Girl: Drink your coffee.
Sullivan: (speaking as he drinks from his cup) Can ya act?
The Girl: What'd you say?
Sullivan: I said, can ya act?
The Girl: Sure, I can act. Would you like me to give you a recitation?
Sullivan: Go ahead.
The Girl: Skip it. My next act will be an impersonation of a young lady going home. On the thumb.
Sullivan: In that outfit?
The Girl: How about your own outfit?
Sullivan: Well, I mean, haven't you got a car?
The Girl: No, have you?
Sullivan: No, but...
The Girl: Then don't get ritzy. And I'll tell ya some other things I haven't got. I haven't got a yacht, or a pearl necklace, or a fur coat, or a country seat, or even a winter seat. I could use a new girdle, too.
Sullivan: I wish I could give you some of the things you need.
The Girl: (She laughs) You wouldn't be trying to lead me astray, would you? You know, the nice thing about buying food for a man is that you don't have to laugh at his jokes. Just think. If you were some big shot like a casting director or something, I'd be staring into your bridgework, saying, 'Yes, Mr. Smearkase; no, Mr. Smearkase; not really, Mr. Smearkase. Oh! Mr. Smearkase, that's my knee!' (To the cook) Give Mr. Smearkase another cup of coffee. Make it two. (To Sullivan) Want a piece of pie?
Sullivan: No thanks, kid.
The Girl: Why, Mr. Smearkase, aren't you getting a little familiar?
Sullivan: Look. (The cook fills his cup.) Thanks. Look. If you wanted to stay in Hollywood a little longer -
The Girl: I don't want to stay in Hollywood a little longer. I've used up all my money, all my going-home money -

Sullivan proposes staying in an out-of-town friend's place for a couple of weeks (his own place!), to allow her more time to get her big break in the film capital. He assures her that there are no strings attached, but promises that he has some possible influence: "I know you don't know who I am, but I used to know a few people around here, and this guy's really out of town." He is worried that unsavory thugs might pick her up hitchhiking, and then proposes borrowing his 'friend's' car. She is unsure of his veracity: "Now, you're just gonna get yourself in trouble." To help her, Sullivan leaves to get his own automobile, promising that he will return before she can say "that big director's name - Lubitsch." The scene dissolves to them both riding in the front of his handsome coupe. She asks if she could be dropped off - in the Midwest: "Would Chicago be too far?...that's a little better than halfway and I could easily hitch a ride out of there." Sullivan quips: "Where do you live, in Bermuda?" Naturally, she assumes that he has probably stolen the car that "belongs to a picture director - a guy named Sullivan." Absent-minded, he can't remember whether he left a note (for his valet and butler) saying that he borrowed it - he is also miffed that Sullivan is a director she's never heard of.

In gales of laughter, she recalls one of the silly scenes from one of Sullivan's pictures she has seen, Hey Hey in the Hayloft, without knowing he is the director of the film she rates as "wonderful" but "stupid":

Oh, that was a wonderful scene. Of course it was stupid, but it was wonderful. Who directed that picture?

He tests his argument about comedic films with her: "Don't you think with the world in its present condition with death snarling at you from every street corner that people are a little allergic to comedies?" Sullivan confesses that he "used to be a picture director" that made pictures "along educational lines." She criticizes filmmakers who get too preachy:

The Girl: ...There's nothing like a deep-dish movie to drive you out in the open.
Sullivan: What are you talking about? Film's the greatest educational medium the world has ever known.

The Girl reflects about her bad luck on her last day in Hollywood now that she has met a "washed-up" film director. After being pulled over by two motorcycle cops, Sullivan has to clear up the "hullabaloo" about charges of stealing his own car in the Beverly Hills Police Station. He is positively identified by his butler and valet and promptly let go - the Girl is also released from custody with him, with a tongue-in-cheek joke about the movies and her non-descript name:

The Police Sergeant (J. Farrell MacDonald): How does the girl fit in this picture?
Sullivan: There's always a Girl in the picture. Haven't you ever been to the movies?

On their way to his mansion in the back of his own limousine, it dawns on her that he is "the washed-up director" - a man who is richer than his tramp outfit indicates. Sullivan is discouraged by his own bad luck and his fateful return to Hollywood: "No matter where I start out for, I always end up right back here in Hollywood." He takes her home and promises to repay her kindness with a breakfast of ham and eggs. The rich furnishings of his mansion bring out her cynicism: "Where is the swimming pool? You must have a swimming pool." There's also an outdoor dining room and barbecue, tennis court, grape arbor and grove. Turning furious for fooling her and "making fun of a poor girl" by impersonating a "washed-up director," she pushes him into the pool: "Hey you big fat-head...That's for your swimming pools and your tennis courts and your limousines and your barbecues. That's for making fun of a poor girl who only tried to help you, you big faker..."

He grabs her by the ankle and pulls her into the pool - she screams as she hits the water. Shortly after, they are eating an elegant breakfast served poolside by the butler and valet. While their clothes are drying, each wear white terry-cloth bathrobes. The Girl shows off her gorgeous legs. She mocks his "noble experiment" - a rich Hollywood director experiencing what it's like to be poor: "You've taken all the joy out of life. I was all through with this kind of stuff. I mean, I knew I'd never have it. But there was no envy in my heart. I'd found a friend who'd swiped a car to take me home. And now I'm right back where I started...Just an extra girl having breakfast with a director - only I didn't used to have breakfast with them. Maybe that was my trouble."

To his surprise, she pleads to join up with him on the road because she alone has the kind of experience and know-how that would help him with his project:

You don't know anything about anything. You don't know how to get a meal. You don't know how to keep a secret. And you can't even stay out of town...I know fifty times as much about trouble as you ever will. And besides, you owe it to me. You sort of belong to me. When you're a hobo, I found you...Please!

Following her convincing arguments, he reluctantly agrees to have her accompany him to tour the underside of America.

Second Voyage or 'Movie' of Sullivan's Travels:

Incongruously, the two are driven by chauffered limousine to the outskirts of the freight yard to board the "five forty eight" freight train dressed as tramps. The shiny limo sits amidst tramps at the freight yard. The Girl is disguised as a boy - her long (peekaboo) blonde hair is tucked under a boy's cap and she wears oversized cover-up clothing as his "frail" or "beazle" (female companion):

Sullivan: Why don't you go back with the car? You look about as much like a boy as Mae West.
The Girl: All right, they'll think I'm your frail.
Butler: I believe it's called a beazle, Miss, if memory serves.

A realistic, subjective camera angle from the moving train shows them joining about a hundred transient tramps who swarm and converge toward the train and scamper onto the boxcars. He boosts her into a cattle car with straw covering the floor - as the train picks up speed, she laboriously helps yank him aboard. Two weary old tramps sit with no comment and watch from a corner of the car. The newcomers are observed and judged as "Amateurs." When they attempt to strike up a friendly conversation with the two hoboes and ask about the labor situation - Sullivan's first real encounter with tramps - the vagrants spit disgustedly and leave. The smelly old freight car, normally filled with hogs, causes Sullivan to have fits of constant sneezing from "hog fever." She is impatient and asks about their journey - where they're going and how long it will take to get there. He reminds her of their mission: "Haven't you got enough imagination to pretend we're broke, hungry, homeless, drifting in despair? Now let's just sit here and try to feel like a couple of tramps."

But the reality of their uncomfortable, distasteful conditions quickly becomes apparent. During their first cold night on the road, Sullivan is revolted and becomes chivalrous toward his female companion, suggesting that she return home. When he refuses to join her, she is committed to remain with him on the road, fearing that he will get into trouble. When he admits his intended goal is precisely that - she admires his tenacity: "Gee, I like that about you. You're like those knights of old who used to ride around looking for trouble..." The next morning, they talk about the real face of poverty and how authentic bums struggle to feed themselves. Sullivan admits: "There's a lot of suffering in this world that ordinary people don't know anything about."

After noticing a town approaching that has a lunch stand, Sullivan jumps off the train and runs alongside the car for a while, as he coaxes The Girl to jump. When she quits hesitating, she takes a wild leap into his arms and they end up sprawled across the ground on a straw heap. In the Busy Bee Lunch roadside stand, they end up ordering two coffees. But as Sullivan reaches for his ten cents and finds himself broke, he realizes he spent it a few days earlier in "that owl wagon." The Girl hungrily eyes a clear plastic container covering a mound of doughnuts for dunking. The counterman (Roscoe Ates) notices, slaps down two coffee cups and plates, uncovers the doughnuts, and gives each of them a sinker with an irritable comment: "I'll never get rich." Sullivan promises the generous man future riches: You're a little richer than you were. Hundreds of miles from everything, cut off from the world, I taste of human kindness. I'll never forget it as long as I live. What town is this?"

As fate would have it, Sullivan raises the inflection in his voice when he realizes they are in Las Vegas, Nevada where the land yacht is scheduled to wait for him. The counterman points out back to the odd-looking deluxe bus. Once inside the land yacht, Sullivan makes good on his promise to reward the counterman. The messenger of the land yacht runs into the lunch stand and hands the counterman a wad of cash (a hundred dollars), explaining to the astonished man that it's an anonymous gift: "Here's something for ya...It's Christmas, so long."

Although Sullivan wants to travel the "hard way" toward Kansas City, the studio doctor forces him to convalesce for three days due to his fever and cold. The Girl takes advantage of food, a hot shower, and makeup. Positive evaluations of Sullivan's travels are sent to the studio chiefs: "This whole thing is doing him a power of good." Again aggravated for being returned to the safety and comfort of Hollywood, Sullivan rhetorically reflects about how he is repeatedly trapped in Hollywood and the movies (his first two voyages have portrayed varying film genres: one comical, one melodramatic): "It's a funny thing how everything keeps shoving me back to Hollywood or Beverly Hills, or this monstrosity we're riding in. Almost like, like gravity as if some force were saying, 'Get back where you belong. You don't belong out here in real life, you phony you.!'...Maybe there's a universal law that says, 'Stay put. As you are, so shall you remain.' Maybe that's why tramps are always in trouble. They don't vote. They don't pay taxes. They violate the law of nature...But nothing is gonna stop me. I'm gonna find out how it feels to be in trouble, without friends, without credit, without checkbook, without name. Alone." The Girl persists in wanting to be with him: "And I'll go with you." He replies: "How can I be alone if you're with me?"