Classic Photos of Bob Hope, American Wisecracker

Bob Hope was a man of contradictions. One of the most popular and best-loved American comedians of the 20th century, he was, in fact, born in England. (He became a U.S. citizen in 1920.) A model of “wholesome entertainment” during the glory days of his career, he was reportedly an incorrigible womanizer, bedding some of the most famous actresses in Hollywood (including Lucille Ball, Paulette Goddard, Jane Russell, Dorothy Lamour and others) while married to his wife of 69 years, Dolores. Alternately slick and bumbling onscreen and in his countless stage acts, Hope was enough of an athlete to enjoy a brief boxing career in his teens, fighting under the name “Packy East” and winning more bouts than he lost.

Throughout it all, Hope rattled off endless — and often painfully hokey — one-liners with a sense of timing that most comedians could only envy. His style, of course, didn’t suit everyone. Christopher Hitchens, for example, wrote a withering assessment for Slate in 2003, titled “Hopeless,” in which he raked the Hope, who had recently died at age 100, over the coals.

“Eye-rolling and wolf-whistling,” Hitchens wrote, “are among the weakest forms of crowd pleasing. . . . [A]nd Hope never stretched or challenged an audience in his life. For him, the safe and antique moves were the best, if not the only. The smirk was principally one of risk-free self-congratulation.” And those were among the kinder of Hitchens’ criticisms.

But for so many others — and especially, perhaps, the countless men and women he entertained during his shows for American troops around the world across six decades — the man born Leslie Townes Hope in London in 1903 was a quintessential funnyman. In fact, if he’d never done anything but the hugely popular series of “Road” pictures that he made with Bing Crosby and Dorothy Lamour, Hope’s place in the Hollywood pantheon would still have been secure.

Liz Ronk, who edited this gallery, is the Photo Editor for LIFE.com. Follow her on Twitter @lizabethronk.