Steve McQueen

Bike: Triumph TR6

Not only is Steve McQueen on the list for being one of the coolest bikers of all time but he will be on the top of any list on the coolest men in the world. McQueen was an avid motorist with plenty of bikes and cars under his name. In his most famous movie ‘The Great Escape’ he bikes his way through some of the most iconic scenes in cinema. He was a big bike head outside of movies too, even inspiring James Dean to buy a motorcycle. Mr cool looked the part on any bike but was always loyal to Triumph bikes, and we can’t blame him.

Valentino Rossi

Bike: Yamaha R1

We all know this man, the 9 times MotoGP World Champion honed his biking skills around the narrow country roads in a small Italian village and went on to become the most second successful motorbike racer of all time, but he’s still active into his 40s. The Italian is probably one of the fastest and most skillful bikers in the world. What isn’t cool about this man? He’s laid back, always smiling and an all-round nice guy.

Sonny Barger

Bike: Harley Davidson Stroker

Outlaw. Felon. Author. Actor and founder of the notorious biker gang – the Hell’s Angels, the Oakland Chapter. This infamous character is no stranger to trouble and has become somewhat of a celebrity. Sonny Barger is the most famous Hell’s Angel and has been in the gang since their 1960’s heyday. Hunter S Thompson made him the focus of his book ‘Hell’s Angels’ where he famously beat the shit out of Hunter S Thompson, who was no doubt high and causing trouble himself.

Sam Childers

Bike: Custom Built Chopper

You may have not heard of this man. Sam Childers is a bad guy turned good. The former outlaw biker turned his back on a life of crime to help those in need over in South Sudan, he became known as the ‘Machine Gun Preacher’ as he was always equipped with a massive gun. He was portrayed by Gerard Butler in a movie about his life. He was a member of the Outlaws motorcycle club, a former heroin addict and even married a stripper. The man managed to climb out of that crime-ridden rabbit hole to go on to win the Mother Teresa Award for Social Justice. How incredible is that!? He and his wife founded a care center in South Sudan where they have 300 children in their care.

Gregory David Roberts

Bike: Royal Enfield

Australian, Gregory David Roberts wrote the book Shantaram which is based on his turbulent life from a drug addict to a bandit to drug smuggler to convict to escaped criminal to Mumbai gangster to gentleman author. He states in his book – ‘riding a motorcycle is velocity as poetry’. This man had one hell of a life and he was riding through it on his beloved canary yellow Royal Enfield. His book is well worth a read, rumor has it they are making a movie on this man’s life with Johnny Depp set to play the Aussie biker.

James Dean

Bike: Triumph TR5 Trophy

This man needs no introduction. James Dean has become an icon for being cool, his photo is seen in cafes, clubs, and homes around the world. The young James Dean lived fast and died young. He was cool beyond his years and took a love towards Triumph motorcycles thanks to Steve McQueen. He certainly liked to ride in the fast lane, famously dying in a Porsche 550 Spyder at the age of 21. Dean’s Triumph bike still exist today and can be seen at the James Dean Museum in Fairmount, Indiana.

Thomas Edward Lawrence

Bike: Brough Superior SS100

T.E. Lawrence, aka “Lawrence of Arabia” famously died in a motorcycle crash. The man was also the subject of one of the greatest films in cinema history. He was an archaeologist, army officer, military theorist, diplomat, writer, and motorbike enthusiast. The movie ‘Lawrence of Arabia’ is based on his wartime efforts and follows on to his untimely death in the Dorset countryside on his Brough Superior at the age of 46.

Evel Knievel

Bike: Harley-Davidson XR-750

One of the most famous people in the world and probably the most famous name – Evel Knievel. The stunt rider attempted over 75 ramp to ramp motorcycle jumps in his time, filling out stadiums such as Wembley, where over 90,000 people watched his fearless stunts. He had a troublesome childhood, getting into motorbike chases with the police and eventually getting locked up. He got into stunt riding to help support his family after watching the Joie Chitwood show. The rest his history. The man has been inducted into the motorcycle hall of fame and rightfully so.