The Five Keys are generally regarded by aficionados of 1950s R&B vocal group harmony as one of the finest groups to ever record in this genre. They are best known for their Capitol recordings of "Wisdom of a Fool," "Close Your Eyes," "Ling Ting Tong," and "Out of Sight, Out of Mind." But in collectors' circles their earlier recordings for Aladdin such as "My Saddest Hour," "Glory of Love," and "Red Sails in the Sunset" are even more highly revered and sought after. The group originally consisted of two sets of brothers; Rudy and Bernie West and Raphael and Ripley Ingram all hailing from Newport News, VA, part of the "Hampton Roads" area. This region had a rich history of high-caliber vocal music and had previously spawned great vocal ensembles like the Golden Gate Quartet and Norfolk Jazz Quartet. The West and Ingram brothers initially took on the name the Sentimental Four and soon decided to show off their talents by entering a local amateur program at the Jefferson Theater. After winning three consecutive weeks of amateur contests at the Jefferson, they were invited to perform at the prestigious Apollo Theater in New York City, where they also won.