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      Chaplin was one of Hollywood’s first true auteurs. He did everything. He acted, directed, produced, and wrote. He even recorded the soundtracks for his films. He was a perfectionist and it shows. His films are still loved almost a century later, and his Tramp character has become a film icon.

      Though he was known best for his silent films, such as City Lights and Modern Times, Chaplin had a rapier wit, even on his deathbed. After a priest had read him his rites, ending on “May the Lord have mercy on your soul,” Chaplin chimed in:

      “Why not? After all, it belongs to him.”

      Bob Hope (1903–2003)

      Hope lived to be one hundred years old, and, in true Bob Hope style, he used this as fodder for a one-liner, famously musing, “You know you’re getting old when the candles cost more than the cake.”

      From his first films in the mid-1930s to his last USO tours in the early 1990s, Bob Hope was a ubiquitous presence on American stage and screen. He appeared in more than sixty films, including the famous Road movies with Bing Crosby. He hosted the Academy Awards nineteen times, and he golfed with eleven presidents—including one notable occasion when he rounded out a foursome with Ford, Clinton, and Bush.

      It is safe to say he had pretty much seen it all in his century as an actor, singer, dancer, golfer, comedian, host, USO performer, and all-around entertainer. So his last words were fitting indeed:

      “Surprise me.”

      Bing Crosby (1903–1977)

      The other half of the road-movie duo, Bing, was truly one of a kind. His awards list includes an Oscar, three stars on the Hollywood Walk of Fame, a Cecil B. DeMille Award, and the first ever Grammy Lifetime Achievement Award. He was a beloved actor, and he had a voice that has inspired generations of crooners and set a bar for Christmas carols that still hasn’t been beat.

      To say that Crosby was an American institution would be an understatement. He was in the top ten for box-office sales for fifteen years, while also managing to record twenty-three albums that went gold or platinum. He did it all with an approachable, nice-guy image that resonated with pretty much everyone on earth, and still does to this day.

      Crosby died doing what he loved. After playing a round of golf in Spain, a game he reportedly lost by one stroke, Bing suffered a massive heart attack on his way back to the clubhouse. His last words:

      “That was a great game of golf, fellas.”

      Josephine Baker (1906–1975)

      Baker did it all. She was an actor, singer, dancer, writer, activist, and French Resistance agent. She lived in a castle, spoke at marches alongside Martin Luther King Jr., and was awarded medals for her part in World War II.

      At age sixty-eight, she was starring in a retrospective of her work in Paris, a show attended by Mick Jagger, Diana Ross, and Liza Minelli. A couple of days after the show, she died of a cerebral hemorrhage and was found at her home, surrounded by clippings of rave reviews. The last words anyone remembers her saying were as she left a party in her honor:

      “Oh, you young people act like old men. You are no fun.”

      John Barrymore (1882–1942)

      John was born into a theatrical family, a family that he would propel to new heights as one of the early stars of the screen. While Barrymore first rose to fame on the stage, taking on some of Shakespeare’s most famous roles, he was best known for his light comedies and charming on-screen demeanor. Due to a combination of his famous good looks and stage-trained voice, he was one of the most successful actors during the transition from silent films to talkies.

      He was also perhaps the first bad boy of Hollywood. His famous quips include, “You can only be as good as you dare to be bad,” and “Sex: the thing that takes up the least amount of time and causes the most amount of trouble.” His last words:

      “Die? I should say not, dear fellow. No Barrymore would allow such a conventional thing to happen to him.”

      Joan Crawford (1905–1977)

      In the 1930s, Joan Crawford quickly moved from being Hollywood’s “It Girl” to being Hollywood’s “It Woman.” She played characters that were as smart, hardworking, and as tough as she was, and boy was she tough. Crawford famously butted heads with just about everyone in the business and had a legendary rivalry with Bette Davis.

      One of Crawford’s most famous lines is, “You have to be self-reliant and strong to survive in this town. Otherwise you will be destroyed.” And nobody lived this credo like Joan.

      Crawford’s sharp tongue and fierce independence never faltered, even at the end. In Joan’s last moments, her maid dropped to her knees to pray by her bedside, but Crawford cut the pleas short:

      “Damn it! Don’t you dare ask God to help me!”

      Donald O’Connor (1925–2003)

      An incredibly prolific star of stage, film, and television, O’Connor is perhaps better known for his supporting roles than for his many leads. The talented song-and-dance man had a lot of memorable moments in a lot of great films, but the one he is best known for is his award-winning role as Cosmo Brown in Singin’ in the Rain, which features his hilarious performance of “Make ‘Em Laugh.”

      Despite his impressive list of credits, O’Connor has been called one of the most underrated stars of his era. On his deathbed, he joked to his family:

      “I’d like to thank the Academy for my lifetime achievement award that I will eventually get.”

      (Sadly, he has yet to receive it.)

      Douglas Fairbanks (1883–1939)

      The swashbuckling star of silent films such as Robin Hood and The Mark of Zorro was at one time known as the king of Hollywood. Fairbanks shone in the era of silent films, becoming the epitome of a matinee movie star with his many turns as lovable costumed rogues, pirates, thieves, and outlaws.

      In the 1920s, his stardom went through the stratosphere when he married Mary Pickford. The pair are commonly recognized as Hollywood’s first power couple and were met by legions of adoring fans everywhere they went.

      Sadly, Fairbanks’s time at the top was short, as his health and fame declined during the talkie era, and he and Pickford separated in the mid-1930s. He died in 1939 of a heart attack at his home. His last words:

      “I’ve never felt better.”

      Sir Laurence Olivier (1907–1989)

      There is perhaps no other actor that has had the combined impact on both stage and screen as Sir Laurence Olivier. Olivier dominated the West End, helped build the Old Vic into the respected company it is today, and was the founding director of Britain’s National Theatre. He then went on to star in more than fifty films, as well as several television shows.

      While Olivier played all kinds of roles, he is best known for his work as a Shakespearean actor. Sir Laurence played every great role the Bard ever put to paper. Being a thespian was so ingrained in Olivier’s DNA that Shakespeare inspired his final words. On his deathbed, when a nurse who was trying to moisten his lips got overzealous with the water, Olivier rebuked her, saying:

      “This isn’t Hamlet, you know. It’s not meant to go

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