Bob Hope was the kind of entertainer who only comes along once in a lifetime. Spanning the decades, he worked through just about every era of the 20th century. Hope grew up doing his best vaudeville routine and ended up performing far and wide with the USO during World War II and the wars in Korea, Vietnam, Lebanon, Iran, and Iraq. In later life, he slowed down a bit, but he still found time to perform both in movies and in person. 

Frank Sinatra’s very name seems synonymous with legend. Sinatra grew up in hardscrabble Hoboken, New Jersey, and rose to prominence as one of music’s first superstars. While becoming one of the best-selling artists of all time, he remade popular music in his own image. From his crooning days on a street corner in Hoboken to his waltzing across the world stage, the swagger of Frank Sinatra was unmistakable.

The British Empire comprised a bewildering collection of colonies, dominions, protectorates, and mandated possessions that spanned the planet. This was the largest empire in world history, at its peak ruling over more than 400 million people and covering almost one-quarter of the total land mass of the Earth.

Bing Crosby was a real legend. Celebrated across the country and beyond, he was essentially America’s first superstar. With catchy tunes, a catchy name, and a laid-back, charming personality that everyone just seemed to love, Crosby was a star both on and off stage.

Margaret Thatcher, famously known as the “Iron Lady” due to her tough-as-nails personality, was not only Britain’s first female prime minister, but one of the most influential political leaders of the 20th century. She commanded the spotlight at a crucial moment in both British and world history. Although she had her problems along the way—dealing with the Cold War, incursions at the Falkland Islands, and attacks by the IRA, at one point almost losing her life in the process—she rose to the occasion.