Amy Winehouse was one of the most iconic voices of her generation. Born in London in 1983, she rose to fame with her soulful, jazz-inspired music, and became a household name with hits like “Rehab” and “Back to Black.” However, behind her success laid a life of personal struggles and addiction that ultimately led to her tragic death at 27-years-old.

Little Richard was an incredible performer and musical pioneer who revolutionized music for generations to come. For just about anyone else, such words might sound like hyperbole, but for Little Richard, it’s the pure and simple truth. Little Richard, with his jumpy driving sound and innovative vocalizations, certainly earned his title as the “Architect of Rock and Roll.”

With his fiery piano-playing style and powerful stage presence, Jerry Lee Lewis enjoyed a meteoric rise to fame. Although his time as a relevant artist was comparably brief, that short time in the sun was nothing short of revolutionary. While his run lasted, Lewis played a pivotal role in forging what would become classic rock and roll and rockabilly.

Even half a century after his death, Humphrey Bogart remains one of the most iconic actors of all time. The epitome of class and cool, he embodied the ultimate tough guy—and no one wore a fedora quite like him. “Bogie” began life under uncertain circumstances, born to parents addicted to drugs and disorder, but he would rise above these difficulties to become a star. From Broadway to Hollywood, he became a top-billed actor, the likes of which the world has rarely seen.

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.