James Bond’s longtime friend and CIA compatriot. He’s been portrayed by many different actors who took a number of approaches to the character. The first on-screen take, in the 1954 TV adaptation of Casino Royale, was actually Australian actor Michael Pate, portraying a British intelligence operative named Clarence Leiter alongside an American James Bond. Producers Albert R. Broccoli and Harry Saltzman hired Jack Lord to play the first Felix Leiter in Dr. No. The film’s tropical climate must have agreed with him, because he went on to spend most of his acting career in Hawaii as American detective Steve McGarrett in the television series Hawaii Five-O.

Lord was succeeded in the part by Canadian Cec Linder (Goldfinger), who was the quintessential 1960s suit-and tie agent; Rik Van Nutter, a lanky, prematurely gray tropical Leiter (Thunderball); Norman Burton, another by-the-book suit-and-tie operative (Diamonds Are Forever); David Hedison, the debonair New England Leiter (Live and Let Die, Licence to Kill); Bernie Casey, in an underwritten role as the first African American Leiter (Never Say Never Again); and John Terry, the youngest-looking Leiter ever, who seems like a kid off a Southern California beach (The Living Daylights). Most recently, Jeffrey Wright is intelligent and classy as the second African American to take on the role of Leiter; introduced as the American card player at the Texas hold’em tournament in Casino Royale, he’s since returned in Quantum of Solace and No Time to Die.

Leiter’s most central role in the series is Hedison’s turn in Licence to Kill, when on the day of his wedding to Della Churchill (Priscilla Barnes), he’s thrown into a shark pool by ruthless drug lord Franz Sanchez (Robert Davi). Leiter’s mutilation—he loses his left leg below the knee—and Della’s murder prompt James Bond (Timothy Dalton) to break away from the British Secret Service and stage his own revenge scheme.