Throughout history, crime has shaped America in unsettling ways, and the individuals behind these crimes have left an indelible mark on society. While mugshots may serve as visual records of their downfall, the real stories lie in the lives and actions of these notorious figures. From ruthless gangsters to cunning serial killers, these criminals have fascinated and horrified the public in equal measure.
1. Al Capone (1939)
Al Capone, a kingpin of organized crime, dominated the Chicago underworld during Prohibition, controlling a vast bootlegging and racketeering empire. His reign of crime eventually came to an end when he was convicted of tax evasion in 1931. Despite his fearsome reputation, Capone’s health deteriorated behind bars due to syphilis, and he spent his final years in Florida, far removed from his once-powerful empire.
2. John Dillinger
A charismatic bank robber and master of escape, John Dillinger was idolized by some during the Great Depression. His string of daring heists and shootouts with police made him a legend, but his luck ran out in 1934 when he was abused and killed by federal agents outside the Biograph Theater in Chicago.
3. Bonnie & Clyde
Clyde Barrow and Bonnie Parker were partners in both crime and life, leading a gang that robbed banks and evaded police for years. While they gained fame for their romanticized outlaw image, their violent encounters with law enforcement ended in a brutal ambush in 1934, leaving them riddle with ullets in their car in Louisiana.
4. Charles ‘Pretty Boy’ Floyd
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Once considered a Robin Hood figure by some, Charles Floyd was a bank robber who operated during the Great Depression. Though admired for allegedly destroying mortgage documents to help struggling farmers, his violent crimes ultimately led to his death at the hands of the FBI in 1934.
5. Machine Gun Kelly
Not to be confused with the modern musician, George ‘Machine Gun’ Kelly was a Prohibition-era gangster involved in bootlegging, armed robbery, and the infamous kidnapping of oil tycoon Charles Urschel. He was captured in 1933 and spent the rest of his life in Alcatraz.
6. Ted Bundy
A cunning and manipulative serial killer, Bundy used his charm to lure unsuspecting women to their deaths. Convicted of multiple murders across several states, he twice escaped custody before his final capture. Executed in 1989, his crimes continue to be studied as some of the most chilling in American history.
7. Charles Manson
8. John Wayne Gacy
By day, Gacy was a respected businessman and community figure; by night, he preyed on young men and boys, luring them to their deaths. Convicted of 33 murders, his case remains one of the most horrifying in U.S. History. He was executed in 1994, but his crimes still haunt true crime enthusiasts today.
9. Jeffrey Dahmer
A serial killer and cannibal, Dahmer’s crimes were so gruesome they continue to shock the world. Between 1978 and 1991, he murdered 17 men. Captured in 1991, he was sentenced to life in prison but died at the hands of a fellow inmate in 1994.
10. Whitey Bulger
A feared Boston crime boss, Whitey Bulger ran a criminal empire that engaged in racketeering, extortion, and murder. He was also a longtime FBI informant, using his connections to eliminate rivals. After going into hiding for 16 years, he was finally captured in 2011. He died in prison in 2018.
11. Lucky Luciano
A key architect of modern organized crime, Charles ‘Lucky’ Luciano was instrumental in creating the Commission, a governing body for the American Mafia. He was convicted and later deported to Italy, where he remained active in the criminal underworld until his death in 1962.
12. Richard Ramirez
Known as the ‘Night Stalker,’ Ramirez terrorized California in the 1980s with a spree of brutal home invasion and murders. His Satanic symbolism and remorseless attitude made him infamous. He was sentenced to death but died in prison in 2013 from complications related to cancer.
13. Ted Kaczynski (The Unabomber)
A Harvard-educated mathematician turned domestic terrorist, Kaczynski waged a nearly two-decade-long mail bomb campaign targeting those he believed were advancing technology at the expense of human freedom. His manifesto led to his capture in 1996. He spent the rest of his life in prison before dying in 2023.
14. Lee Harvey Oswald
Forever linked to one of America’s most shocking assassinations, Oswald was arrested for killing President John F. Kennedy in 1963. Before he could stand trial, he was shot and killed by nightclub owner Jack Ruby, fueling decades of conspiracy theories about the true nature of the assassination.
15. Frank Abagnale
Unlike the violent criminals on this list, Frank Abagnale was a master con artist who pulled off some of the most daring fraud schemes in history. Posing as a pilot, doctor, and lawyer, he evaded authorities for years before being captured in 1969. After serving time, he reformed and later worked with the FBI to combat fraud, inspiring the film Catch Me If You Can.
