Can You Name All These Real and Fictional Cowboys and Outlaws from One Image?


By: Jody Mabry

6 Min Quiz

Image: Test Hero Credit

About This Quiz

WANTED: Dead or Alive: An Expert on Cowboys and Outlaws!

Let’s take a trip back to the Wild West and the American Frontier. This popular period of time certainly had its fair share of characters, both in history and on the silver screen. There were, of course, the “good guys” — the legends of the law, the sheriffs, lawmen, scouts and sharpshooters. But, as everyone knows, you can’t have the good without the bad. Perhaps the most famous and notorious of all were the gunslingers, outlaws, those villains of the Old West. These men were known for merciless killing, raids, train robberies, gunfighting, and just plain doing whatever the heck they wanted.

The history of the cowboy, both in myth and in reality, begins in Texas, where cattle freely grew without having to worry about attackers. There were over five million of them by the end of the Civil War. So, the Golden Age of the cowboy began, which ranged from 1866-1886. As beef prices increased up North, the Texan cowboys expanded to the West. Here the image of the brave, free-spirited, broncobuster living in constant risk was born and immortalized forever as an American folk hero. Wearing wide-brimmed hats, a bandana handkerchief, and of course boots with ornate spurs, the cowboy has been deeply embedded in folklore as a true American hero — so much so, in fact, that it is almost impossible to tell the difference between myth and fact.

Are you starting to get feel a bit of that nostalgia for the wild and wooly American West yet? Then saddle up and read on. Who are your favorite cowboys and outlaws? If you rooted for the good guys, you probably wished you were fighting outlaws with the Lone Ranger or gunning down villians at O.K. Corral with Wyatt Earp. Good guys too boring for you? Do you dream of partnering with the Butch Cassidy, robbing a train with the James Gang or cattle rustling with Billy the Kid instead? Or, how about both? Either way, let out a “YEE-HAW,” because you’re about to ace this quiz.

Many of the bad guys traveled in gangs, such as the Wild Bunch Gang, led by the notorious Butch Cassidy. Named after the original Wild Bunch, aka the Doolin-Dalton Gang, these guys operated out of the famous Hole-in-the-Wall pass in Wyoming. They’re most famous for robbing banks, trains, and stores, as well as for killing sheriffs and lawmen. You’ve probably heard of the Regulators too, which included the famous gunslinger Billy The Kid, who’s notorious for killing eight men. There’s also tales of the deranged outlaw Clay Allison, who killed a suspected murderer, cut off his head, and took it to a bar to share a drink! His gravestone allegedly reads, “Clay Allison. Gentleman. Gun Fighter. He never killed a man that did not need killing.”

So, you’ve heard the stories, but can you recognize these iconic cowboys and outlaws from an image? Get ready to earn your spurs as a Wild West pro. Pull the trigger and start the quiz!

Which cowboy or outlaw is in this image?

Bonnie and Clyde are arguably the most famous outlaw couple of the 20th century. They were ambushed and killed by a small posse in 1934. The coroner reported that Clyde had been shot 17 times and Bonnie 26, however, any of the shots would have resulted in death.


How about this one?

Billy the Kid, born Henry McCarty (aka William H. Bonney) is arguably one of the most notorious outlaws in American history. He began his life with petty theft, then moved to cattle rustling, and eventually to murder, of which the total number killed widely varies. Billy was supposedly killed by Sherrif Pat Garrett; however, rumors persist that he lived for decades longer.


Do you know this cowboy-outlaw?

The Lone Ranger is the most well-known fictional Wild West character. He and his sidekick, Tonto, have been featured in movies, radio shows, television series and comic books.


Name this one, now!

By the age of 15, Annie Oakley was an expert sharpshooter. She joined the Buffalo Bill's Wild West Show, where she became an international celebrity.


Ride high and name this one!

Gene Autry, known as "The Singing Cowboy," was a popular entertainer on TV and radio shows. He would go on to own multiple TV and radio stations as well as a minor league baseball team. He died of lymphoma at the age of 91.


Who is this cowboy or outlaw?

In the movies, Steve McQueen played Tom Horn, who held several roles in the Old West, from hired gunman to Pinkerton detective. With 17 murders under his belt, Horn would later be executed for the murder of a 14-year-old boy. He was hung one day shy of his 43rd birthday.


Who's this one?

Roy Rogers was a popular singer and Western actor. He appeared in over 100 films. A Roy Rogers "mocktail" includes cola, grenadine and a cherry.


What's the name of this cowboy or outlaw?

Born Robert Leroy Parker, Butch Cassidy was the leader of the Wild Bunch Gang out of Wyoming. The gang focused on train and bank robberies, After years of harassment by the Pinkerton Detective Agency, Cassidy and two friends moved to Bolivia, where they were reportedly killed in a shootout with the law in 1908.


How about this cowboy or outlaw?

Geronimo was the leader of an Apache band of Indians who fought the U.S. and Mexican militaries for over three decades. He would later become an icon as he traveled to fairs throughout the country


And this one?

"Shane" is a movie about an old gunfighter who just wants to settle down. The role was played by Alan Ladd.


Who is this person in this image?

The Apache Kid was an Apache scout and renegade in the American Southwest. His birth and death are mysteries, with varied claims.


How about the one in this image?

John Hardin is one of the most lethal and notorious gunfighters in the American West. Hardin reportedly admitted to 42 murders, however, newspapers at the time reported between 25 and 27 murders. He was shot and killed after serving 17 years of a 25-year prison sentence.


And in this image?

Tom "Black Jack" Ketchum was a cowboy who quickly turned to train robbery. He was a member of the Hole-in-the-Wall Gang and later hung in 1901.


Familiar with this cowboy or outlaw?

Scurlock was a founding member of the Regulators during the Lincoln County War. He rode with Billy the Kid, then later retired to a peaceful and respectable life.


Spell out the name of this cowboy!

Casey Tibbs was a cowboy and actor. He died at age 60, while watching the 1990 Super Bowl.


Can you identify this cowboy or outlaw in the image?

"Bad Chuck" Roberson was a cowboy and an actor. Similar in stature to John Wayne, Roberson played Wayne's stunt double for almost 30 years.


Who is this cowboy or outlaw in this photo?

Doc Holliday was a dentist, gambler and drinker, well known for the gunfight at the O.K. Corral. He was friends with famous lawman Wyatt Earp. He died at the young age of 36 from tuberculosis.


Which indigenous cowboy or outlaw is this?

Cherokee Bill was an outlaw who ravaged Indian territory until his capture. He is notably known for his quote before hanging. When asked if he had anything to say, he answered, "I came here to die, not make a speech." He got his wish 12 minutes later.


Can you name this fictional cowboy or outlaw?

Rio was a character in the movie "One-Eyed Jacks." It was the first and only film directed by Marlon Brando.


Which cowboy turned outlaw is this?

Henry Newton Brown, like many, went from lawman to outlaw. He was a member of the Regulators, riding with Billy the Kid. He was killed by a lynch mob in his mid-twenties.


Who are these cowboys or outlaws?

The Bloody Espinosas were led by Felipe Espinosa. Many claim Felipe was the first American serial killer, with an estimated 32 murders in a year and newspapers of the time going as high as 60. He was killed by Thomas Tobin. Felipe's head was later on display in a jar filled with alcohol at a Colorado newspaper.


Which hair-famous cowboy or outlaw is this guy?

Curly Bill was an outlaw cowboy who later came into conflict with the Earps. He was accused of participating in Morgan Earp's murder and was later killed by Morgan's brother, Wyatt.


Who's this cowboy or outlaw dude?

Sam Bass was a famous train robber. He would later be betrayed by a gang member and would die a day after a shootout with the Texas Rangers.


What's the name of this guy?

James Averell was hung, along with his partner, Ellen Watson, by the Bothwell Cattle Baron Faction. His is one of many deaths that led to the Johnson County War.


How about this man?

Cole was the eldest member of the four-brother Younger gang. He practiced guerrilla warfare during the Civil War, and would later ride with the James brothers.


Who's this guy?

Zip was reportedly a member of the Doolin gang. He was tracked down and shot by deputies, eventually dying in jail from his wounds. He was made a sort of side show while in jail by people eager to see the infamous outlaw.


Which cold-killing cowboy or outlaw is this?

Killer MIller is known by several names. He reportedly killed up to a dozen men in gunfights and was eventually lynched by a mob, angry over his assassination of a U.S. Marshal.


Which Cassidy-partnered cowboy or outlaw is this?

The Sundance Kid was a famed train robber and partner with Butch Cassidy. He and Butch would ride to Bolivia to hide from the Pinkerton Detective Agency, where it is believed he died in a gunfight.


Can you name this cowboy or outlaw from the picture?

BIll Picket was a cowboy and entertainer. He had 12 siblings and was born to a former slave.


This cowgirl outlaw is named what?

Little is known of Pearl Hart's life. However, she was a Canadian-born outlaw who committed one of the last stagecoach robberies in America. After a prison sentence, she essentially disappeared from history.


Even cowgirls get the blues, so name her!

Belle Star was an infamous outlaw who rode with the James-Younger gang. She was later murdered, the killer still unknown.


Which assassinated cowboy or outlaw is in this photo?

Jesse James was a notorious outlaw who ravaged banks throughout the Midwest, with his brother Frank and friends, the Younger brothers. He was murdered by his friend, Bob Ford, who hoped to collect the bounty.


Which older cowboy is in this image?

The Ringo Kid is an outlaw character, played by John Wayne in the 1939 movie, "Stagecoach." He would get caught up in a gunfight and later escape capture at the end of the movie.


Who is this cowboy turned sheriff?

Jason McCullough was played by James Garner in the 1969 movie, "Support Your Local Sheriff." The movie centers on McCullough, who became sheriff to make some extra money. However he becomes a better sheriff than he thought he'd be.


Which time-conscious cowboy is this?

Will Kane was a town Marshal in the movie "High Noon." The character was originally played by Gary Cooper in the 1952 movie, and later by Lee Majors in a made-for-TV sequel.


Where is my John Wayne, here playing which cowboy?

Tom Doniphon is a character in the movie, "The Man Who Shot Liberty Valance." He was played by John Wayne. The movie takes place primarily in flashback.


What's the name of this character?

Joel McCrea played Steve Judd in the movie Western, "Ride the High Country." The film received critical acclaim, both in the United States and Europe -- the last of McCrea's movie to receive such honors.


How about this cowboy character?

Will Penny is a character in a movie of the same name, played by Charlton Heston. The movie follows an aging cattle hand who becomes involved in the lives of a woman and her son who were abandoned.


Name this cowboy character.

Will Lockhart is the lead character in the movie, "The Man from Laramie." The movie is loosely based on the cattle wars of Lincoln and Johnson Counties in the 19th-century American West.


Which comedic cowboy is this?

Curly Washburn was played by Jack Palance in the hilarious movie, "City Slickers." Palance played the typical hardcore cowboy, responsible for two men from the city looking for adventure in their lives.


Which dramatic cowboy is this?

Robert Duvall played Gus McCrae in the popular series, "Lonesome Dove." Despite massive acclaim, the series lost the 1989 Outstanding Miniseries Emmy Award to "War and Remembrance."


Who is this elderly cowboy?

Robert Duvall played Gus McCrae in the critically acclaimed miniseries "Lonesome Dove." The amazing cast also included Tommy Lee Jones (as Woodrow Call), Danny Glover, Anjelica Huston, Steve Buscemi, and Diane Lane.


Who is this TV cowboy?

Pernell Roberts played Adam Cartwright in the TV series, "Bonanza." He appeared in 200 of the show's 430 episodes.


Who is this gambling cowboy?

Bret Maverick is a popular card-shark character originally played by James Garner on the TV show "Maverick." The series was unique in that it alternated the lead character role between Bret and his brother Bart Maverick, played by Jack Kelly, as well as a cousin named Beau.


Who is this true-to-life cowboy-outlaw?

Waite was a cowboy in John Tunstall's clan when Tunstall was killed. He would later join the Regulators and, along with Billy the Kid, fight in the Lincoln County War, where he was killed.


Explore More Quizzes

About HowStuffWorks Play

How much do you know about dinosaurs? What is an octane rating? And how do you use a proper noun? Lucky for you, HowStuffWorks Play is here to help. Our award-winning website offers reliable, easy-to-understand explanations about how the world works. From fun quizzes that bring joy to your day, to compelling photography and fascinating lists, HowStuffWorks Play offers something for everyone. Sometimes we explain how stuff works, other times, we ask you, but we’re always exploring in the name of fun! Because learning is fun, so stick with us!