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What could be more enticing, more adventurous, and more romantic than a tale of outlaws in love?  Maybe you’re familiar with the lives of Bonnie and Clyde, the love-struck public enemies who led a bloody tour across America during the Great Depression.  They’ve left a legacy that has been immortalized in film, song, and stage, and set a precedent for romantically-charged crime sprees.  Here’s a list of some more notorious crooked couples — some sweet, some sad, and some downright horrific.

Bonnie Elizabeth Parker and Clyde Chestnut Barrow

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Our list begins with the most notorious romantic outlaws of all time: Bonnie and Clyde.  The pair met in Texas in 1930, right before Clyde was sent to jail for burglary.  Using a gun that Bonnie snuck in to the prison, he escaped, was rearrested, and eventually received parole in 1932.  By 1933, the pair had assembled a gang of five — including Clyde’s brother Ivan and his wife Blanche — who committed a gaggle of bold robberies.  Because of the sensational nature of the crimes (and the strength of Bonnie and Clyde’s love for each other), they made headlines from coast to coast.  Most of their crimes were larceny-related: carjackings, gas-station holdups, and, most famously, bank robberies.  It is estimated that they were responsible for the deaths of more than a dozen people, at least nine of them policemen.  Their rampage came to an abrupt halt in May of 1934, when they were shot down by police beside a stretch of highway near Sailes, Louisiana.

Belle and Sam Starr

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Back in frontier days, Belle Starr was one of the more notorious cattle rustlers of Indian Territory.  Starr (born Myra Maybelle Shirley) was a childhood friend of the infamous train robber Cole Younger, and often let him and his friends Frank and Jesse James hide out on her farm.  In 1880, she married Sam Starr and started a ranch in what is currently Oklahoma (it’s also when she started going by the nickname, “Belle”).  From there, the Starrs controlled a number of illegal operations, including bootlegging and planning and harboring “rustled” cattle and horses.  In 1883, Belle and Sam were each sentenced to a year in prison for horse theft — a surprisingly lenient sentence for a case presided over by Fort Smith, Arkansas’s “Hanging Judge” Isaac Parker.  Their romance ended when Sam Starr was killed in a gunfight in 1886.  Belle took up with one of his relatives, and was shot in the back while carrying home some groceries in 1889.  It was that year that a writer named Richard K. Fox wrote Bella Starr, The Bandit Queen, or The Female Jesse James, hurtling her into infamy.

Doc Holliday and Big Nose Kate

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Mary Katherine Horony Cummings, a Hungarian immigrant, and John Henry Holliday, a dentist (and, more notably, a gambler, gunfighter and tough guy) met in 1876 in Texas frontier country, fell in love, and settled together in Tombstone, Arizona.  Mary Katherine, who garnered the nicknames “Rowdy Kate” and “Big Nose Kate,” was said to have operated a bordello in the town, while John (Doc) Holliday made boatloads of money playing blackjack.  Nefarious deeds were afoot.  Doc and Kate were good friends with the lawman Wyatt Earp, and together Earp and and Holliday instigated what would become the most well-known battles in the history of the Old West—the gunfight at the O.K. Corral, in which thirty bullets were said to have been discharged in thirty seconds.  Both Doc and Big Nose Kate (who was supposedly out of town during the fight) were charged with murder, but both were exonerated.

Charles Starkweather and Caril Ann Fugate

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Raymond Fernandez, a former merchant marine and British Intelligence agent, met Martha Beck after responding to a personal ad she left in the newspaper.  Fernandez had made a habit of responding to “Lonely Hearts” ads, meeting with the women, and robbing them or forcing them to sign over their property.  Beck, a former undertaker who weighed more than 200 pounds, fell madly in love with him and became an eager participant in his scams.  Posing as his sister-in-law, she accompanied him to meet with lonely women, marry them, and steal their possessions.  Finally, in January of 1949, they murdered Janet Fay, one of the lonely women they were scamming.  A month passed before they shot Delphine Downing to death in front of her two-year-old child.  They were arrested at the end of February, and the press latched onto the story, dubbing them “The Lonely Hearts Killers.”  Fernandez later blamed his behavior on a head injury he sustained on a boat trip, and claimed that he had been trained in voodoo and black magic in a subsequent prison stay.  In 1951, Beck and Fernandez were both executed by electric chair.

Myra Hindley and Ian Brady

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These lovebirds from Greater Manchester in Northern England led a much darker criminal career than Bonnie and Clyde.  The couple, led by Brady (who was supposedly obsessed with committing a “perfect murder,” lured five adolescents to their death.  Hindley would bait the young people into her car by asking for help (she asked her first victim to help her locate a missing glove), then take them to a secluded location, where Brady was waiting to slit their throats.  In four of the five murders, Brady also sexually assaulted their victims.  The couple buried the majority of their victims in distant Saddleworth Moor, which earned them the nickname “The Moors Murderers.”  Hindley had became enamored with Brady when she was just 18 years old; together they read works by Marquis de Sade, as well as Dostoevsky’s classic perfect-murder-and-repentance novel Crime and Punishment.  Both were sentenced to life in prison.

Fred and Rosemary West

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The Wests were another deadly couple hailing from England, one whose actions were even more inhumanly brutal than Brady and Hindley’s.  In their youth, both members of the married couple were victims of frequent sexual abuse and incest.  When Fred met Rosemary, he was 27, a father, and married to a former prostitute; she was 15.  They moved in together, and while Fred spent six months in prison for theft, Rosemary murdered his stepdaughter, Charmaine— purportedly because she refused to cry when Rosemary abused her.  The Wests were married in 1972.  Fred encouraged his wife to sell her body, and she eventually had seven children, almost all from different fathers.  In late 1972, they hired a young woman to nanny their children, and then raped her.  The following year, Fred began raping his daughter, eight-year-old Anne-Marie, and continued to do so until she was 1979 when she suffered an ectopic pregnancy and managed to escape.  Finally, in 1992, Fred and Rosemary’s activities were discovered and both were charged with rape.  During the investigation, police discovered human bones buried at their house in Gloucester.  It is commonly believed that Fred and Rosemary had murdered 10 victims together, including Fred’s ex-wife and both of the children from his former marriage.  Fred West hanged himself a few years later; Rosemary is currently serving a life sentence.

Karla Homolka and Paul Bernardo

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Like Fred and Rosemary West, Karla Homolka and Paul Bernardo were a young married couple who corroborated on the murders of three young girls.  The first was Karla’s 15-year-old sister, Tammy, who they drugged with animal tranquilizers.  While she was unconscious, Paul raped her, and she eventually choked on her own vomit; she never woke up from the episode.  The next was Leslie Mahaffy, who they held hostage and assaulted for more than 24 hours before killing her.  Their final victim was Kristen French, who they brutally assaulted for three days before strangling her to death.  Because the defendants were an attractive young married couple, their story made headlines across their native Canada, and were even dubbed “the Ken and Barbie of murderers” by national newspapers.

The Dougherty Siblings

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While it’s true that these cross-country murderers weren’t necessarily a couple, their familial relations makes their story just as captivating.  Stripper Lee Grace Dougherty and her brothers Ryan and Dylan, lived in Zephyrhills, Florida, just North of the Tampa Bay area.  Their misadventure began in early August 2011, when a they sped away from and fired shots at a police officer who had tried to pull them over for speeding.  From there they headed to Georgia, where they robbed a bank wielding high-powered artillery.  Their semi-successful getaway came to an abrupt halt a week later, when police at a restaurant outside of Walsenberg, Colorado cornered them.  After attempting to escape, they were arrested.  Searching through their car, investigators found a machine pistol, two assault rifles, and a handgun.

Roy and Jessica Fritts

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This romantic duo may not have been as bright or brilliant as Bonnie Parker and Clyde Barrow, but they were just as human.  Roy and Jessica Fritts met through a prison pen pal program (Roy was in jail for attempted murder; Jessica was serving time for a bank robbery), and the pair married while they were still incarcerated in an Oregon state prison.  Last month, the Fritts broke Roy’s parole in order to take a trip to Nevada.  They hitched a ride with a stranger, murdered him, dumped his body on the side of the road, and took off with his van.  After police managed to blow out the van’s tires, the Fritts fled on foot and ended up at the residence of an old man living in Summit County, Utah.  Again, they committed murder for a car — but this car had manual transmission, which neither Roy nor Jessica knew how to operate.  The car went on the fritz, and the Fritts went into police custody.

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