Did you flinch, did you care?
Did he look, did he stop and stare
At your brand new hair?"
If you want the audience to quickly place the timeframe that a work takes place in, the easiest way is to sprinkle it with the aesthetic that the timeframe is famous for. In the case of The Roaring '20s, few things are as iconic as The Flapper, and all flappers (at least, according to Hollywood) have bobbed hair, whether the Louise Brooks shingle kind, the Josephine Baker Eton crop kind, the Clara Bow Quirky Curls kind, or the femme, wavy Joan Crawford kind.
A character wearing such a hairstyle will more often than not also be The Flapper, although she could alternatively represent another type of socially progressive woman. Because this was a time frame where women were expected to be subservient to men and Stay in the Kitchen, defying Long Hair Is Feminine was a powerful visual statement that the woman in question didn't subscribe to the then-accepted notions of a "woman's place." One side effect of this is that after the sexual revolution, the hairstyle has also become associated with dominatrices because of its outward authoritativeness.
In Japan, a short bob (usually paired with a kimono) is a nostalgic shorthand for the Taisho and pre-war Showa eras, when this haircut was massively popular with young girls.
Bobbed hair continued to be a trend in the 1930s, although the sleek shingles and Eton crops were pushed aside in favour of more feminine styles such as pin curls and Marcel/finger waves, which then be replaced by updos and pageboy bobs by the end of the decade. One simple way to distinguish 1920s and 1930s hairstyles is that 1920s hairstyles focused on sleek and masculine, while 1930s hairstyles focused on wavy and feminine.
- Being set in the Duckburg of the twenties, the Italian series "Le Strabilianti Imprese di Fantomius-Ladro Gentiluomo" (The Amazing Feats of Fantomius-Gentleman Thief) has this as a recurring haircut.
- LuLu Romanov of Nikolai Dante sports this kind of haircut. This is likely deliberate given the strip's Anachronism Stew setting.
- In Chassis, Caddie, Tommy Tropic's Fembot chauffeur, has Robot Hair resembling a stylised shingle bob: very fitting for the book's Art Deco aesthetic.
- Blondie: Blondie, who was a flapper before marrying Dagwood, is known for her early 30s-style curly bob, which she still wears to this day.
- The title character of Chic Young's earlier strip Dumb Dora sported a hairstyle that blended the styles of Josephine Baker and Louise Brooks.
- Buck Rogers has femme fatale Ardala. Even the short-lived 1970's revival of the comic strip, which generally tried waaaaaay too hard to be contemporary, still let her keep her iconic haircut. The TV series did not, though.
- The title character of the 1920s-era comic Ella Cinders was well-known for her straight bob.
- 1921 comedy Leap Year has female lead Mary Thurman wearing the bob several years before it was popularized by the likes of Colleen Moore and Louise Brooks.
- In the film The Roaring Twenties a montage features a woman getting a bob haircut to help establish the setting.
- Cutting It Short, a Czech film from The 80s directed by Jiří Menzel, based on a novella of the same name by Bohumil Hrabal. Maryshka is a young wife of a local brewery manager. She's extremely lively and spirited, completely unashamed to publicly do things which others only think or do in private. She has gorgeous long honey blond hair, wavy and thick. Her hair is admired by the whole town and they compare it to its memorable sights. At the end of the movie, she decides to have her hair cut like Josephine Baker. note This is the last straw for her husband who spanks her in front of a board of directors of the brewery.
- Thoroughly Modern Millie
- Most women Millie sees in the street at the beginning of the film wear bob haircuts. It's one of the fashion things that Millie gets obsessed with.
- Millie bobs her hair as part of her Makeover Montage. Other things she does include getting a new shorter dress and a Nice Hat, and trying to invoke Petite Pride as her silhouette is not perfect for the year 1922.
- Subverted with her friend Miss Dorothy who has cute curly hair. She's a very feminine girly girl character and not overly lively. Millie convinces her to bob her hair at one point; however, she then meets Millie's boss who falls in love with her and tells her that cutting such gorgeous hair would be a sin.
- Lots of the characters wear this hair style. Not surprising since it's set in The Roaring Twenties.
- Velma Kelly, a Vaudeville star, has beautiful raven black hair and she wears the slick version.
- Roxie Hart has a curly blond bob cut. People start copying her, even the prison guard Mama Morton. She would love to become a famous star.
- Daisy Buchanan and Jordan Baker both wear shingles in the 2013 film adaptation of The Great Gatsby; shingles popped out in 1923, a year after Gatsby was set.
- Why Be Good? is a film from 1929 about a flapper, so the bob haircut is a must.
- Gosford Park is set in 1932 but most of the upper class ladies sport bobs, since the earlier parts of a decade usually have fashion holdovers from the previous one.
- Fantastic Beasts and Where to Find Them, as befitting its setting in 1920's New York City, features the Goldstein sisters, who have two different takes on this hairstyle. The straight-laced brunette Tina wears her hair in a straight bob, while bubbly blonde Queenie has a bob full of curls.
- Sirens uses this trope in an odd way. The protagonist Estella wears her hair like this in contrast to the Rapunzel Hair of Norman Lindsey's models. As she's quite repressed, the haircut serves as an indicator that she wants to break out of that.
- In Easy Virtue which has a Genteel Interbellum Setting, both Larita and Sarah sport bobs. It's used to show how more modern they are in their thinking, compared to the rest of the area still grieving World War I.
- In the film version of Nine, Judi Dench sports this haircut as the costume designer Lily. The film is set in the 60s, so Lily would have been the right age to be a flapper in her youth. It shows that she's a Cool Old Lady who Guido can rely on.
- Surprisingly uncommon in The Cat's Meow (given its setting of 1924 Hollywood), though Didi—who is probably the most stereotypically flapper amongst the cast—does sport one.
- The first chapter of the Anno Dracula novella "Vampire Romance", set in 1923, is called "Genevieve Bobs Her Hair", in imitation of Fitzgerald. Genevieve gets a bob as part of fitting in to the new era.
- F. Scott Fitzgerald's short story "Bernice Bobs Her Hair", from 1920. The idea of a girl wanting to bob her hair makes her very attractive to the boys in town.
- Old Kingdom: Sabriel, who grew up in Ancelstierre, a Fantasy Counterpart Culture of early 20th-century Britain, is described as having this hairstyle in her first appearance, although the original cover art doesn't reflect this.
- In Pop!: The Invention of Bubble Gum by author/illustrator Meghan McCarthy, a mother and daughter with 1920s bobbed haircuts are shown on one page blowing bubble gum bubbles. Justified since bubble gum was invented in 1928 and the scene is intended as a historical depiction.
- A plot point in the Tommy and Tuppence story "The Sunningdale Mystery" - Tuppence points out that a woman with bobbed hair is unlikely to have stabbed a man with a hatpin and later extends this to concluding that the murderer was a man trying to frame her.
- Phryne Fisher, being a thoroughly modern miss and part of the fast set, naturally sports one. She attempts to persuade her companion Dot to get one as well, but Dot, who is suspicious all things modern, steadfastly refuses and keeps her long braid.
- Buffy the Vampire Slayer - in Willow's dream in "Restless", a play is being held. Buffy is dressed and coiffed like she's starring in Chicago, while Riley is dressed like a singing cowboy, and Harmony is dressed as an alpine milkmaid - all playing in Death of a Salesman.
- In Charmed, the episode "Pardon My Past" had Phoebe returning to the Roaring Twenties to relive her past life as a witch who was tempted to use her powers for evil by a demon she fell in love with. In her past life, Prue was a popular photographer with a sleek bob. The other two sported another hit of the era — the finger curls.
- Doctor Who:
- "The Unicorn and the Wasp": Robina Redmond, aka "The Unicorn" and Agatha Christie sport these. Donna, having changed into period-appropriate dress, instead puts her hair up.
- "Mummy in the Orient Express": Clara averts the Changed My Jumper trope by dressing in The Flapper bob cut, Gorgeous Period Dress and a Beauty Spot. All this for a guy she's supposedly breaking up with. (This also crosses over with Sci-Fi Bob Haircut because she's on a replica of the '20s Orient Express built in the far future.)
- Downton Abbey:
- In series 2, at the end of World War I, Lady Mary Crawley idly threatens to bob her hair. However, she is quite conservative and keeps her gorgeous raven hair long.
- In series 3, Lady Sybil bobs her hair. She is the most progressive of the Crawley sisters. She is interested in politics, supports women having the vote, wears trousers, consorts with servants, trains as a nurse to volunteer in the war and marries a socialist Irish chauffeur.
- Lady Rose wears a fashionable curly bob with headbands. She represents the new breed of "Bright Young Things", who delighted in shocking society with their antics. Rose carries out her most shocking antics in Series 4, she loses the radical haircut for a wavy, halfway-to-shoulder-length look halfway between a bob and a more traditional cut.
- Lady Mary gets a racy new bob in series 5. Her very campy hairdresser kept flattering her and the new look in general through and through, but as soon as she is out, he shares his true sentiments.
Hairdresser: At least she can carry it off most of them look like bald monkeys.
- Daisy the kitchen maid attempts to give herself a bob in the series finale. Emphasis on attempt. Luckily for her, the rest of the staff are able to fix it.
- Miss Fisher's Murder Mysteries:
- Phryne Fisher wears her hair in a sleek shingle bob, befitting the late-1920s setting of the series and Phryne's own status as The Flapper.
- Dr. Elizabeth "Mac" McMillan has a wavy bob and is a notably progressive woman, a medical doctor who normally dresses in three-piece suits.
- In a Halloween Episode of Sabrina the Teenage Witch the gang are forced to live out an Agatha Christie style murder mystery. Morgan sports this type of haircut, complete with flapper dress - placing the illusion in the 1920s. Sabrina, Hilda and Zelda in their costumes all sport variations of this hairstyle too. Roxie meanwhile as Morgan's character's maid, does not have this.
- In The Supersizers Eat... The Twenties, Sue Perkins, the host, gets a bob haircut during her makeover (she usually wears somewhat sloppy short hair). When she first sees herself in the mirror, she cries: "I look like an evil doll!" The truth is that twenties flapper look of "the young and beautiful elite" suits her perfectly, even though she's not a classic beauty.
- Z: The Beginning of Everything depicts Zelda Fitzgerald getting hers as part of an Important Haircut. After an exhausting lunch with the Bankheads, and Scott trying to make her fit in with them by picking out new clothes, she gets a bob and starts wearing a flapper dress.
- Journalist Tae Asakura from Raidou Kuzunoha vs. The Soulless Army and Raidou Kuzunoha vs. King Abaddon has bobbed hair. The game is set in Japan in The Roaring '20s and she considers herself a "modern woman", to the point where her pen name "Kichou Asakura" is an in-universe tribute to pioneering feminist Raicho Hiratsuka.
- Lackadaisy: Ivy's shingle haircut is supposed to be visual shorthand for her post-secondary, pro-feminist education and behavior. And she's definitely a flapper.
- Problem Sleuth exists in a indistict time filled with an assortment of period cliches aimed largely at parodying the Film Noir genre. That Hysterical Dame and Nervous Broad both have flapper bobs (and jaunty hats) should come as no surprise.
- Flannery from Templar Arizona: her hair and 1920's outfits are used to indicate the alternate history setting where people who casually dress in the fashions of prior decades are a visable subculture.
- In The Legend of Korra, the bob is featured on some female characters as part of the Far East meets The Roaring '20s setting. One of Tahno's Fangirls wears the style◊, while young Jinora combines it with a Prim and Proper Bun. Korra cuts her hair into a messy bob in the final season. Opal has a bob as well. A scene that featured the three of them in a row led to the Fan Nickname "The Bob Squad".
- My Little Pony: Friendship Is Magic, episode "Rarity Takes Manehattan" has Coco Pommel, the Manehattan stylist. Justified in that she's a reference to Coco Chanel.