1

Tom Sawyer

Image: Daniel Chekalov

We’ll start with an American classic . If Mark Twain is considered "the Father of American Literature" , then it would also be fair to consider Tom Sawyer as the father of many great literary characters. And while it is true that "The Adventures of Tom Sawyer" was heavily overshadowed by its sequel "Adventures of Huckleberry Finn", we have decided to choose Tom over Huck mostly because he was Mark Twain’s first and perhaps most iconic character.

Tom is introduced in the novel as an orphan boy who lives with his Aunt Polly in Missouri. Characterized by his penchant for avoiding work, Tom often uses his cunning and wits to skip school and chores. Perhaps his most famous feat is convincing the neighborhood kids that painting Polly’s fence was immense amounts of fun, and charging them for the privilege of doing his busy work.

2

Captain Ahab

Image: Austin Neill

Herman Melville tackled the issues of fanaticism and the battle between humankind and nature in his 1851 masterpiece "Moby Dick". In that sense, the character Melville chose as a vessel to portray these themes is definitively Captain Ahab, the frantic and monomaniacal captain of the whaling ship Pequod , hellbent on capturing the great white whale Moby-Dick.

While Ahab's obsession is fueled by revenge (since the whale bit off his leg), many critics observe how the captain’s mind doesn’t allow for any other feeling other than his mindless obsession with catching Moby-Dick. In the end, this hatred makes him forget to care for himself and his crew, and in their final battle, the whale drags Captain Ahab’s body beneath the sea.

3

Jack Torrance

Image: Luis Villasmil

Immortalized by Jack Nicholson’s superb performance in the 1980 film adaptation of "The Shining", Jack Torrance is arguably the tortured main character of this iconic horror masterpiece. Jack is a down-on-his-luck writer who gets hired as the winter caretaker of the fictional Overlook Hotel, a historical location in the Colorado Rockies.

Much like Captain Ahab, a big part of "The Shining" focuses on Jack’s fight against his own demons. However, where the Captain fails Torrance succeeds: While the dark presence that rules the Overlook possesses him and makes him attack his family, Jack overcomes these manipulations and sacrifices himself in order to save his wife and son.

4

Hester Prynne

Image: Debby Hudson

Hester Prynne might be the very first American heroin : The protagonist of Nathaniel Hawthorne’s "The Scarlet Letter" faces public humiliation and the disdain of her fellow residents of the Puritan Massachusetts Bay Colony, who force her to wear a red "A" on her clothes after committing the sin of adultery.

Yet, Hester always maintains her dignity and love for her daughter Pearl throughout the rest of her life. In the end, the red "A" that decorates her tombstone is not a reminder of her transgressions, but a monument to her determination.

5

Ignatius J. Reilly

Image: mana5280

Ignatius J. Reilly, the bumbling protagonist of "A Confederacy of Dunces", is no hero. He is more of a man-child, an unemployed and unpleasant buffoon whining about the lack of morality in his birthplace, the beautiful city of New Orleans. However, there’s no denying that Ignatius is a wonderfully crafted character and an essential part of what makes John Kennedy Toole’s novel so unforgettable.

"A Confederacy of Dunces" is, undeniably, a unique book: Its characters are as particular and hilarious as the bizarre situations in which they constantly find themselves. In that regard, Ignatius is the perfect protagonist for this unparalleled masterpiece.

6

Philip Marlowe

Image: Michelle Ding

What image comes to mind whenever you hear the phrase "private detective"? Do you picture a sullen man dressed in a beige overcoat and matching fedora , immersed in intense inner monologues about unsolved cases? Well, if that’s the case, you can thank iconic American author Raymond Chandler for creating the quintessential private detective, Philip Marlowe.

Immortalized by the great Humphrey Bogart in the film "The Big Sleep", this chainsmoking detective is one of pop culture’s most iconic characters and one that has endured as a symbol throughout its 90 years of history.

7

Atticus Finch

Image: David Veksler

Just like Philip Marlowe, many consider Atticus Finch to be the quintessential American lawyer : After all, his character is defined by his honesty and dedication to justice. However, the depth of this character from Harper Lee’s "To Kill a Mockingbird" is not only determined by his morality, but for the unconditional love he feels for his two children, Scout and Jem.

"To Kill a Mockingbird" tells the story of the Finch family, which is intertwined with the prejudice-filled trial of Tom Robinson. Atticus acts as Tom’s defense attorney, as he battles the hateful mob mentality of this 30’s Alabama town.

8

The March sisters

Image: micheile henderson

It would feel wrong to separate the four March sisters - Meg, Jo, Beth, and Amy - from Louisa May Alcott’s iconic novel "Little Women", so we have decided to include multiple characters in this entry. Alcott’s masterpiece describes the lives of these four sisters and focuses on their passage into womanhood.

Set in 19th century Massachusetts, "Little Women" is considered to this day to be one of the cornerstones of American literature . Not only that, many believe that the author was able to create a new form of sentimental literature with this book.

9

Blanche Dubois

Image: Lokesh Anand

Tennessee Williams's "A Streetcar Named Desire" proves itself to be a gemstone of American literature just by the genius in its title: While it might seem completely objective, referring to a real-life New Orleans streetcar line named "Desire", it also perfectly describes the unstoppable passion that involves the characters of this play.

In that regard, this play’s protagonist, Blanche Debois, is definitively unforgettable: A stunning yet down-on-its-luck Southern Belle who moves to her sister’s place in New Orleans. She is considered one of the most iconic characters in theater and was played on uncountable occasions.

10

Dorothy Gale

Image: ActionVance

We’ll end this article with one of the most popular American characters in our country’s history. Few characters are as iconic in pop culture as Dorothy Gale is: Immortalized by Judy Garland’s unforgettable performance, Dorothy’s trip to the wonderful land of Oz will forever be a part of American culture and history.

Perhaps the reason why this character is so memorable is the fact that, at the time when L. Frank Baum’s original book was published, Dorothy seemed to be just like every other American girl living on a farm. In a way, millions of American children were able to join Dorothy throughout her trip through the yellow brick road.

1

Edna Foster and Edith Storey (1911)

Even just thirty years after his death, the figure of Billy the Kid was so legendary that films were already being produced based on his life. The first two, both silent shorts, date from 1911 and share an intriguing peculiarity: both star women.

Billy the Kid was directed by Laurence Trimble and is very loosely based on the life of the famous outlaw. It is, however, believed to be a lost film. Edith Storey , an American actress who had played male characters in films such as Oliver Twist , stars as "the Kid."

The Adventures of Billy , on the other hand, was directed by the great pioneer American motion-picture director D. W. Griffith. In this film, the role of Billy is played by American child actress Edna Foster.

2

Johnny Mack Brown (1930)

American college football player and film actor John Mack Brown was the first to play Billy the Kid in the talkies. He was directed by none other than the great film director and producer King Vidor in 1930's Billy the Kid . This film is a pre-Code Western and tells the story of Billy's escape after avenging his boss and the subsequent manhunt by Sheriff Pat Garret.

Johnny Mack Brown had started his career by appearing in a few minor films until he got his big break with this movie. Unfortunately, his career in mainstream cinema did not flourish, leading him to transition into low-budget Westerns. Eventually, he found significant success as a B-movie cowboy , becoming a beloved figure in the genre.

3

Jack Buetel (1943)

Jack Buetel was an inexperienced actor when tycoon Howard Hughes cast him in his next film, The Outlaw , in 1940. Buetel signed a seven-year contract after Hughes promised him that he would make him a star.

The film faced many difficulties. It wasn’t immediately approved due to its erotic scenes, and although it was officially released in 1943, it was not until 1946 that the public was able to finally see it. Produced during the golden age of the genre, The Outlaw is considered a psychological Western. However, it was not well received by the critics of the time, and Buetel's work was especially bashed. After this, Hughes refused to allow Buetel to participate in other films, and his career never really took off.

4

Paul Newman (1958)

Paul Newman is one of the most celebrated actors of the 20th century and is best known for his roles in several classic Westerns. But did you know that the first Western character Paul Newman portrayed was Billy the Kid? In the mid-1950s, Newman was cast to replace James Dean in The Left Handed Gun after Dean's untimely death. This was the beginning of a series of films about the Old West that the beloved American actor would play throughout his career.

Based on a teleplay by Gore Vidal and directed by Arthur Penn, The Left Handed Gun departs from the classic genre iconography to present the famous bandit much closer to the rebellious and tormented antiheroes of the era. Thus, in this film, the characters are complex and nuanced, questioning and revising the traditional portrayal of the savage outlaw.

5

Clu Gulager (1960 - 1962)

The first television series about Billy the Kid was The Tall Man , which aired on NBC from September 10, 1960, to September 1, 1962. Although we all know that the real story ends with Billy being killed by Pat Garrett, this light-hearted action series focuses on the duo's alleged happier days, when they had more of a father-and-son relationship.

Clu Gulager, born in Oklahoma and the son of a cowboy entertainer, plays Billy. Although he was already 32 years old when cast, the actor earned his well-deserved place in the role. After the success of this series, Gulager worked in other Westerns and later had a second career as a horror film actor. His last appearance on the big screen was in 2019, in Quentin Tarantino's Once Upon a Time in Hollywood.

6

Geoffrey Deuel (1970)

While this is not a film specifically about Billy the Kid's life, he does appear as a supporting character. Starring the legendary John Wayne, Chisum tells the story of the 1878 Lincoln County War, an Old West conflict between rival factions involving some famous gunslingers, including William H. Bonney, better known as Billy the Kid.

In this film, Geoffrey Deuel plays Billy the Kid. Although he had already participated in some television series, Chisum was his debut on the big screen.

7

Kris Kristofferson (1973)

Kris Kristofferson is best known for his career as a country musician and his appearance in the 1976 version of A Star is Born alongside Barbra Streisand. But did you know he also portrayed Billy the Kid? In 1973, he was cast in the revisionist Western film Pat Garrett and Billy the Kid , directed by Sam Peckinpah.

One of the most intriguing aspects of Kristofferson's involvement in this film is that he introduced Bob Dylan to the director. Dylan was initially hired to write the title song, but ended up composing the whole score and even played the role of "Alias." Among the songs Dylan wrote for the film was the iconic "Knockin' on Heaven's Door."

8

Val Kilmer (1989)

American writer Gore Vidal was not pleased with the adaptation of his teleplay for The Left Handed Gun , so he decided to produce his own version. The resulting TV movie premiered on TNT in May 1989, with Val Kilmer cast as Billy the Kid.

Kilmer's version of Billy the Kid is a bit friendlier than his predecessors. He was also the right age for the character, making Gore Vidal's Billy the Kid one of the most historically rigorous accounts of the outlaw's life.

After this film, Val Kilmer's career continued to grow, with standout roles in The Doors and Batman Forever . Billy the Kid wasn’t the only gunslinger he portrayed—Kilmer also famously played Doc Holliday in the 1993 film Tombstone .

9

Dane DeHaan (2019)

American actor Dane DeHaan portrays Billy the Kid in the 2019 film The Kid , alongside Ethan Hawke as lawman Pat Garrett. The physical resemblance between DeHaan—a younger Leonardo DiCaprio lookalike—and the real William H. Bonney is striking, making the Vincent D'Onofrio-directed film not only a fresh take but also one of the closest onscreen renditions of the mythical character.

In an interview, DeHaan said that he accepted the role because he thought it was a very interesting character to play. He also explained that he considered Billy the Kid a victim of the media and explained that the film aims to depict the harsh realities of the Wild West, where survival often drove people to desperate and terrible actions.

10

Tom Blyth (2022 - )

The most recent version of Billy the Kid is played by Tom Blyth, a 29-year-old English actor from Birmingham. Blyth plays the infamous outlaw in the television series Billy the Kid, which premiered on MGM+ in April 2022. Produced by Michael Hirst, the English producer behind hits like The Tudors and Vikings , the series was renewed for a third and final season in 2024.

To prepare for this character, Blyth didn't just read a ton of books about Billy's story; he felt the need to do something more tangible to get into the skin of the famous outlaw. He traveled to Arizona, rented a car, and began a 7-day pilgrimage around New Mexico visiting all the places William H. Bonney had once been. He even visited his grave! His intention was to make the character more palpable and real as opposed to this exaggerated image of the mythical character we are used to.

1

James Dean’s red jacket in Rebel Without a Cause

Image: visualsofdana

James Dean owned the screen in Rebel Without a Cause while wearing a red Harrington jacket . Jim Stark’s rebellious spirit resonated with a generation of teenagers, turning the jacket into a symbol of youthful defiance. That cool, casual style caught on in the ’50s and influenced menswear for years to come.

2

Tom Cruise’s aviator sunglasses in Top Gun

Image: Nitin Dhumal

When Top Gun soared into theaters in the ’80s, sales of Ray-Ban Aviators took off like a jet fighter, reportedly increasing by 40%. Tom Cruise’s confident Maverick made these shades the ultimate symbol of effortless cool .

The latest installment of the franchise once again led to a surge in sales. Worn by pilots and by pop stars, Aviators remain a classic icon of the tough-guy aesthetic.

3

Jennifer Aniston’s Rachel’s haircut in Friends

Image: Ilse Orsel

"The Rachel" wasn’t just a haircut—it was the haircut. Salons were flooded with requests for Jennifer Aniston’s bouncy, layered style .

The irony? Aniston reportedly hated it. But that didn’t stop an entire generation from chopping their locks in pursuit of sitcom-perfect hair .

4

Nancy Sinatra’s go-go boots

Image: Heriberto Jahir Medina

Nancy Sinatra’s "These Boots Are Made for Walkin’"—along with the groovy go-go dancers on "Laugh-In" —made white go-go boots the must-have footwear of the swinging ’60s.

Fun, fashionable, and full of youthful energy , they became a symbol of the era. Every mod girl needed a pair to complete her look and strut her stuff.

5

Marilyn Monroe’s white dress

Image: Stephen Leonardi

A subway grate, a gust of wind, and boom. One of the most famous dresses in movie history was born. Marilyn Monroe’s billowing white halter dress is still a summer fashion inspiration more than half a century later.

Her signature winged eyeliner, red lips, and the Chanel No. 5 she allegedly wore to bed were also picked up by women all over the world.

6

Jackie Kennedy’s pillbox hat & suits

Image: Florida Memory

Jackie Kennedy’s impeccable style captivated the nation. Her elegant suits and perfectly perched pillbox hats turned heads with every public appearance.

Women everywhere sought to emulate her sophisticated, polished look, turning the First Lady into an unexpected fashion icon.

7

Farrah Fawcett’s feathered hair in Charlie’s Angels

Image: Flybynight

An example of one poster that became one million salon appointments. Farrah Fawcett’s feathered waves became the ultimate hair trend of the 1970s, thanks to Charlie’s Angels.

Women flocked to salons, armed with cans of hairspray and dreams of achieving the perfect Farrah flip.

8

Madonna’s lace gloves & layered bracelets

Image: Paolo Sbalzer

Madonna was as much a fashion icon as she was a music sensation. During her Like a Virgin era in the ‘80s , she introduced a bold new style: layered rubber bracelets, rosary beads, lace gloves, and a rebellious attitude. Young girls everywhere embraced her edgy, playful look, making it a defining trend of the decade.

9

Run-D.M.C.’s Adidas sneakers

Image: Rahul Shah

No laces? No problem. Run-D.M.C. turned Adidas shell-toe sneakers into hip-hop royalty . Their song "My Adidas" made the brand explode, and suddenly sneakers with the three stripes were everywhere. Comfortable, stylish, and effortlessly cool—now that’s a trend anyone could get behind.

10

Reese's Pieces in E.T. the Extra-Terrestrial

Image: FlyD

Did you know that in E.T. the Extra-Terrestrial , the beloved alien was originally supposed to be obsessed with M&Ms, not Reese’s Pieces ? Luckily for the latter, Mars turned down the offer to feature their product in a Spielberg movie.

The result? After the movie’s massive success, sales of Reese’s Pieces skyrocketed by 65%. A perfect example of how sweet product placement can be.

11

Etch-a-Sketch in Toy Story

Image: Nong

Sure, Toy Story featured dozens of different toys, but one classic that had been around for decades experienced a major resurgence after the movie’s release.

The Etch A Sketch saw a spike in sales in the ’90s, thanks to its memorable cameo in the Pixar movie. Maybe kids were drawn to its simple shake-and-draw magic , or perhaps parents couldn’t resist a wave of nostalgia.

12

Kurt Cobain’s grunge look

Image: Ralph Rabago

Kurt Cobain didn’t dress for the cameras or the music industry, yet he defined an iconic style in the ’90s. His thrift-store flannels, ripped jeans , and round sunglasses became the uniform of a generation.

Ironically, the grunge aesthetic—born from a rejection of mainstream fashion—became one of the decade’s biggest trends.