1. Ted Bundy
   Ed Gein
2. Al Capone
   Charles Manson

Al Capone was an American crime boss and businessman who rose to power after gaining leadership of the Chicago Outfit. His seven-year reign during the Prohibition era came to an end after he was sentenced to 11 years in federal prison for tax evasion.

1. Baby Face Nelson
   Pablo Escobar
2. Osama Bin Laden
   Billy the Kid

Baby Face Nelson, born Lester Joseph Gillis, was an American bank robber who committed a series of robberies in the 1930s. He died on Nov. 27, 1934, after he was shot by FBI agents, three of whom were killed by Nelson himself.

1. James Earl Ray
   Anthony Spiltoro
2. Jeffrey Dahmer
   Tom Horn

Nicknamed "Tony the Ant," this American mobster was an enforcer for the Chicago Outfit, whose job was to manage and protect the gang's illegal casino profits. He ran the casinos in Las Vegas, Nevada from the 1970s to the 1980s.

1. Pablo Escobar
   Vito Rizzuto
2. Josef Mengele
   Ottis Toole

Also known as Teflon Don, Vito Rizzuto was the head of the Rizzuto crime family and the alleged leader of the Sicilian Mafia in Canada. Beginning in 2003 he was arrested multiple times and at one point served a five-year prison sentence.

1. Carlo Gambino
   Osama Bin Laden
2. Josef Mengele
   James Holmes

Known for being low-key and secretive, Carlo Gambino was a Sicilian-American mobster and former boss of the Gambino crime family. During his lifelong criminal career, he seized control of the Commission of the American Mafia in 1957.

1. Dennis Rader
   David Berkowitz
2. Michael Swango
   John Dilinger

John Dillinger was an American gangster who, along with a group of men known as the Dillinger Gang/the Terror Gang, allegedly robbed twenty-four banks and four police stations.

1. Reinhard Heydrich
   Jesse James
2. Jospeh Colombo
   Dennis Rader

Joseph Colombo was the boss of the Colombo crime family and founder of the Italian-American Civil Rights League, which under his guidance, grew quickly and gained national attention.

1. Osama Bin Laden
   Ottis Toole
2. Pablo Escobar
   Vito Genovese

This Italian-American Mafioso was an enforcer in the American Mafia who rose to power during the Prohibition period. He was referred to as the "Boss of all Bosses" and later ruled over the Luciano crime family, (later renamed the Genovese crime family) for twelve years.

1. Jeffrey Dahmer
   Richard Ramirez
2. David Berkowitz
   Meyer Lansky

This major organized crime figure was known for his strong influence in the Italian-American Mafia. During his nearly 50-year reign, he developed a gambling empire which stretched to Las Vegas, Cuba, The Bahamas and London.

1. Frank Bompensiero
   David Berkowitz
2. James Earl Ray
   Michael Swango

As a Mafia hitman and Caporegime of the Los Angeles crime family, Frank Bompensiero made a name for himself for the numerous murders he committed on behalf of his superiors.

1. Richard Ramirez
   Ted Bundy
2. Mickey Cohen
   Ed Gein

Los Angeles based gangster, Mickey Cohen was the head of the Cohen crime family. During the Prohibition Era, he moved to Chicago where he ran a gambling operation and worked as an enforcer for the Chicago Outfit.

1. John Wayne Gacy
   Richard Ramirez
2. Jeffrey Dahmer
   Stefano Magaddino

Sicilian mobster Stefano Magaddino, nicknamed "The Undertaker," was the head of the New York Buffalo crime family and a charter member of The Commission. He was the longest reigning boss in American Mafia history, having spent fifty years in the Buffalo underworld.

1. Richard Ramirez
   Charles Manson
2. Carmine Galante
   Klaus Barbie

Also known as "Cigar" and "Lilo," Carmine Galante was an American mobster and head of the Bonanno crime family. He was murdered on July 12, 1979, at an Italian-American restaurant.

1. David Berkowitz
   James Earl Ray
2. Louis Campagna
   Michael Swango

Also known as "Little New York," this American gangster spent over thirty years as a high-ranking member of the Chicago Outfit. He passed away on May 30, 1955, having suffered a heart attack.

1. Jeffrey Dahmer
   Richard Ramirez
2. Vincent Gigante
   Osama Bin Laden

Also known as Chin, this New York Italian-American Mafioso was the leader of the Genovese crime family from 1981 until his death in 2005. He spent his early years as a professional boxer, then as a Mafia enforcer of the Luciano family.

1. Jesse James
   Ottis Toole
2. Santo Trafficante Jr.
   Reinhard Heydrich

Considered to be the most powerful mobster, Santo Trafficante Jr. was one of the last old-time Mafia bosses. He passed away at the age of 72 in 1987, one year after escaping conviction.

1. John Wayne Gacy
   Santo Trafficante Sr.
2. Josef Mengele
   Ottis Toole

Sicilian-born mobster, Santo Trafficante Sr., was the head of the Mafia in Tampa, Florida during the 1930s until his death in 1954. He was a well-respected boss with ties to other powerful mobsters such as Thomas Lucchese.

1. Ottis Toole
   Crio Terranova
2. Josef Mengele
   Billy the Kid

Nicknamed the "Artichoke King," this New York gangster was a one-time underboss of the Morello crime family which he founded with his three brothers – Vincenzo and Nicolo Terranova and Giuseppe Morello.

1. Klaus Barbie
   Joe Gallo
2. Andrei Chikatilo
   Reinhard Heydrich

New York City gangster Joe Gallo was a member of the Profaci crime family, later called the Colombo crime family. He was the initiator of the First Colombo War and as a result, was murdered out of revenge on April 7, 1972.

1. David Berkowitz
   Charles Manson
2. Ted Bundy
   Henry Hill

Henry Hill was an American mobster who was affiliated with the Lucchese crime family between 1955 and 1980. To avoid execution from his crew or possible imprisonment, he became an FBI informant who led to 50 convictions of various mobsters.

1. Charles Manson
   Russell Bufalino
2. Michael Swango
   Ted Bundy

Russell Bufalino, also known as McGee and "the Old Man," was a Sicilian-American Mafioso who ruled over the Bufalino crime family from 1959 to 1989. During his time as a crime boss, he played a significant role in the national Costa Nostra criminal organization.

1. Albert Anastasia
   David Berkowitz
2. James Holmes
   Tom Horn

This organized crime figure was one of the most feared hitmen of the Italian-American Cost Nostra era, a reputation which earned him the nicknames "the Mad Hatter" and "Lord High Executioner."

1. Anthony Corallo
   Andrei Chikatilo
2. Michael Swango
   Pablo Escobar

New York City mobster Anthony "Tony Ducks" Corallo was the head of the Lucchese crime family. He passed away on August 23, 2000, after serving 13 years of a 100-year federal prison sentence.

1. James Earl Ray
   Josef Mengele
2. John Wayne Gacy
   Tommy Lucchese

Sicilian-born American gangster Tommy Lucchese, was a founding member of the American Mafia and, after starting out as an underboss, moved up the ranks and soon became head of the Lucchese crime family from 1951 to 1967.

1. Ottis Toole
   Osama Bin Laden
2. Richard Ramirez
   Bugsy Siegel

This Jewish American mobster was considered one of the most feared and infamous gangsters of his day. During this time, he was one of the founders and leaders of the Murder, Inc. and played a prominent role in the development of the Las Vegas Strip.

1. Ed Gein
   Ted Bundy
2. John Gotti
   Pablo Escobar

As the head of the Gambino crime family, John Gotti became one of the most powerful and feared crime bosses in the world. His crime family earned millions of dollar a year through numerous illegal activities such as extortion, drug trafficking and hijacking.

1. David Berkowitz
   Billy the Kid
2. Johnny Stompanato
   Andrei Chikatilo

Former United States marine, Johnny Stompanato Jr., turned to a life of crime, after becoming a bodyguard and enforcer for the head of the Cohen crime family, Mickey Cohen. He was murdered in 1958, after being stabbed to death by actress Lana Turner's daughter, Cheryl Crane.

1. Machine Gun Kelly
   David Berkowitz
2. Charles Manson
   Richard Ramirez

Born George Kelly Barnes, this American gangster was a Prohibition-era gangster whose crimes included armed robbery and bootlegging. His nickname was derived from his favorite weapon, the Thomas submachine gun.

1. Pablo Escobar
   Whitney Bulger
2. Charles Manson
   Andrei Chikatilo

Former organized crime boss James Joseph "Whitey" Bulger was the head of the Winter Hill Gang. After being tipped off by former FBI handler John Connelly, Bulger went into hiding and was arrested sixteen years later on June 22, 2011.

1. Klaus Barbie
   John Wayne Gacy
2. Billy the Kid
   Bugs Moran

Bugs Moran, born Adelard Cunnin, was a Chicago Prohibition-era gangster. As a member of the North Side Gang, he frequently crossed paths with the rival South Side Gang, led by Al Capone.

1. Jeffrey Dahmer
   Osama Bin Laden
2. Billy the Kid
   Roger Touhy

This Irish-American mob boss and bootlegger was well-known for being framed for the fake kidnapping of John Factor, for which he spent 26 years in prison. Shortly after his release, he was murdered by hitmen of the Chicago Outfit.

1. Andrei Chikatilo
   Angelo Bruno
2. John Wayne Gacy
   James Earl Ray

During the two decades spent as the head of the Philadelphia crime family, this Sicilian-American mobster earned himself the nicknames "The Gentle Don" and "the Docile Don" due to his preference for reconciliation over violence.

1. Joe Profaci
   Klaus Barbie
2. Ted Bundy
   Michael Swango

Giuseppe Profaci was an Italian American Mafioso and member of the New York La Cosa Nostra. He, later on, established the Profaci crime family, which he ruled over for more than three decades.

1. Pablo Escobar
   Ronnie Biggs
2. Dennis Rader
   Jim Jones

This English thief was well known for his participation in the 1963 Great Train Robbery. After escaping prison in 1965, he spent the next thirty-six years as a fugitive and fathered four children.

1. John Wayne Gacy
   Paul Vario
2. Andrei Chikatilo
   Josef Mengele

American mobster Paul Frank "Paulie" Vario, was a made man and caporegime of the Lucchese family. As a caporegime, he led his own crew of mobsters in Brooklyn, New York.

1. Josef Mengele
   John Wayne Gacy
2. Ed Gein
   Raymond L.S. Patriarca Sr.

Raymond Patriarca was a longtime boss of the Patriarca crime family; for more than three decades, to be exact. He was one of the most powerful mobsters in the U.S., whose influence extended throughout New England during his reign.

1. Reinhard Heydrich
   Jesse James
2. Frank Costello
   Billy the Kid

This Italian-American crime boss was one of the most powerful and influential mafia bosses, eventually earning the nickname "The Prime Minister of the Underworld." As the head of the Luciano crime family, he owned a large gambling empire which stretched across the United States.

1. Sammy Gravano
   Jesse James
2. Richard Ramirez
   James Colosimo

Born Vincenzo Colosimo, this American Mafia crime boss gained power through petty crimes and creating a chain of brothels. Before his death, he led a gang of criminals which would later be known as the Chicago Outfit.

1. Reinhard Heydrich
   Mad Dog Coll
2. Sammy Gravano
   Klaus Barbie

Vincent "Mad Dog Coll" was an Irish-born American mob hitman during the early 1920s until his death in 1932. He earned his nickname due to the alleged accidental killing of a 5-year-old during a mob kidnap attempt.

1. Pablo Escobar
   Jeffrey Dahmer
2. Ronald Kray
   Reinhard Heydrich

Ronald "Ronnie" Kray was the younger of the Kray twins who were involved in a string of organized crimes alongside their gang "The Firm." As a nightclub owner, he became popular, having interacted with many celebrities and appearing on television interviews.

1. Sam Giancana
   Ed Gein
2. James Earl Ray
   Jesse James

Salvatore "Sam" Giancana was a Sicilian-American mobster who led the Chicago Outfit from 1957 – 1966. Giancana was murdered on the night of June 19, 1975, after being shot in the back of the head and then six more times in his face and neck.

1. Sammy Gravano
   Dean O'Banion
2. Pablo Escobar
   Lucky Luciano

This American gangster was known as the founder and leader of the North Side Gang, which thrived during the Prohibition period. He was a participant in the Chicago bootlegging wars of the 1920s, rivaling Johnny Torrio and Al Capone.

1. Jeffrey Dahmer
   Lucky Luciano
2. Klaus Barbie
   Tony Accardo

This longtime American mobster spent eight decades of his life a member of the Chicago Outfit. During his time with the gang, he started out as a small-time hoodlum, and by 1972 became the final authority of the group.

1. Osama Bin Laden
   Ed Gein
2. Joe Masseria
   Lucky Luciano

Giuseppe "Joe the Boss" Masseria was the boss of the now called Genovese crime family in New York. He was the initiator of the Callamarese War; a bloody power struggle between Joe Masseria and Salvatore Maranzano.

1. Lucky Luciano
   Ed Gein
2. James Burke
   James Holmes

James Burke, also known as "Jimmy the Gent" and "the Irishman," was an American gangster and associate of the Lucchese family, who was believed to be the brains behind the 1978 Lufthansa heist.

1. Ed Gein
   Ted Bundy
2. Reginald Kray
   Charles Manson

English gangster Reginald Kray, who, along with his younger identical twin brother, was involved in a series of organized crime with the help of his gang, the Firm. These crimes included armed robberies, assaults, protection rackets and arson.

1. Danny Greene
   Jesse James
2. Reinhard Heydrich
   Sammy Gravano

This American mobster was well-known for his participation in the war with the Cleveland Mafia which took place throughout the 1970s. He was allied with the Cleveland mobster John Nardi, and eventually set up his own group, the Celtic Club.

1. Pablo Escobar
   Dawood Ibrahim
2. Ted Bundy
   Ed Gein

Not your typical gangster, Dawood Ibrahim was an Indian and designated terrorist who is wanted on various charges including murder, extortion, drug trafficking, targeted killing, and terrorism. As of 2011, he was listed number three on the "World's 10 Most Wanted Criminals".

1. Sammy Gravano
   Owney Madden
2. John Wayne Gacy
   Billy the Kid

Irish-American underworld figure Owen Vincent Madden started his life of crime as a member of the Gopher Gang in New York. He earned his nickname as "The Killer" after the gunning down of an Italian gang rival in the streets.

1. James Holmes
   Lucky Luciano
2. Billy the Kid
   Frank Nitti

Born Francesco Raffaele Nitti, this Italian-American mobster was Al Capone's top henchman who later on succeeded him after his death. As the enforcer, he was in charge of all the strong arm and "muscle" operations.