Travelling Salesman Montage

You can't do it,
So give up now
Whatcha gonna do
When your dough runs out?
Ain't it a drag?

—Homestar Runner, Strong Bad Email #117, "montage"

A person facing repeated rejection or unsuitability, i.e. via speed-dating, door-to-door selling or people being interviewed.

Will typically show the person approaching various people with increasing desperation, and always ends with a rapid-fire series of doors being slammed in his face, women slapping him, getting laughed at, etc.

Subtrope: Terrible Interviewees Montage.

No real life examples, please; Real Life does not have montages.

Examples of Travelling Salesman Montage include:

Comic Books

Several story arcs in Powers include a montage sequence of people responding to questions about the current case. Unlike most of the examples, these sequences end in a success (i.e. Walker and Pilgrim finally find somebody who has a useful lead).
Atomic Robo. In "The Ghost of Station X", a team from Tesladyne is trying to track down an entire house that was covertly shipped in one piece from New York. There are no records remaining (erased by the conspiracy), but they figure someone involved in a move like that must not have forgotten. After a series of increasingly incredulous responses from movers, skycaps, stevedores, pilots and shipping clerks when they ask if they'd helped move a whole house by air freight, one actually says yes.

Film

The Muppets Take Manhattan - Kermit & company trying to get a talent agent to book their musical.

Dr. Teeth: You can't take no for an answer! You can't take no for an answer! You can't take no for an answer! No, no, no!

Tommy Boy, of course. It also had a reverse montage where they quickly get people to buy their parts.
Groundhog Day features a sequence in which Phil Connors is attempting to use the knowledge he's gaining in multiple repetitions of the day to seduce his coworker Rita. At first, he seems to be making progress, as he learns what mistakes not to make, but he's ultimately unable to recreate the exact circumstances of the day on which he got the closest to succeeding, leading to a montage of him being slapped in the face at different points during the day until he finally gives up.
The Secret of My Success. After a rapid-fire sequence of rejections, Michael J. Fox declares, "Whatever the exception is, I can fix it. I can be older, I can be taller, I can be anything." The interviewer asks, "Can you be a minority woman?"
In Cool Runnings, a variety of businesspeople laugh when asked to sponsor the Jamaican bobsled team.
The protagonist of Goodbye Lenin and his co-worker go through one of these selling satellite dishes. They eventually succeed.
The movie of Bridget Jones's Diary has a montage of Bridget going for several unsuccessful job interviews in TV. When she admits "I've got to leave my current job because I've shagged my boss", she is hired at last.
In Edward Scissorhands, Peg repeatedly strikes out while trying to sell Avon products to her neighbors. After having yet another door shut in her face, she gets the idea to drop by the creepy castle on the hill where she discovers Edward.
Inverted in Secondhand Lions, where an early scene shows many salesmen trying to get the brothers McCann to buy their wares...only to get shot at by the brothers.

Live-Action TV

Buffy the Vampire Slayer: Anya has a scene like this when she's trying to convince various women to wish for vengeance on Xander after he left her at the altar.
A Terrible Interviewees Montage happens in Stargate SG-1 when Cam Mitchell, shortly after we first meet him, is trying to find replacements of the title team.
Malcolm in the Middle: Malcolm finds himself subjected to this as he tries to raise funds for a charity 10K. The montage suddenly cuts from people slamming the door in his face to people happily signing up to pledge money, and then we see Malcolm giving a thumbs up from Stevie's wheelchair, while Stevie himself sits at the curb, looking pissed.
Waterloo Road.
Played straight (and promptly made fun of) in Hired, a short film by Chevrolet shown on Mystery Science Theater 3000.

Newspaper Comics

Happened to Linus once in a Peanuts Sunday strip where he goes door-to-door around the neighborhood to tell people about the Great Pumpkin. The strip itself has six people slamming doors in his face as soon as he tells them why he's there; according to the letter he writes to the Great Pumpkin afterwards, he actually visited 50 houses and it happened at every one of them.

Web Animation

Of course, the salesman montage in the Strong Bad email "montage", featuring The Cheat and a Wagon Fulla Pancakes, backed with the snippet of song quoted above.

Web Comics

In The Order of the Stick prequel "On the Origin of PCs", Roy is subjected to one of these when interviewing for his final party member.
Used in the introduction of Ow, My Sanity, to show how much David's life sucks.

Western Animation

King of the Hill has this when Peggy is a saleswoman attempting to sell energy supplement snacks. She gets the door slammed on her from every house she goes to and skips Bill's house who is willingly to buy her products.
Daffy Duck goes through one of these at the beginning of the Looney Tunes movie Daffy Duck's Quackbusters.