In 1931 the sixteen-year old Jack Smith and two friends found themselves replacing The Rhythm Boys (Bing Crosby, Al Rinker and Harry Barris) at the famous Coconut Grove. Jack, as the soloist for the trio, known as The Three Ambassadors, got to sing all the Bing Crosby numbers and the trio's popularity grew. Jack began to get solo offers and the trio eventually broke up in 1939. With his friendly, engaging voice, Jack was perfect for radio and became a regular on The Prudential Hour, where Jack's solo spot allowed him to perform the popular hits of the day. Fan mail started to roll in, and many of the letters commented that he sounded like he was smiling and the show's host, latching on to this, was soon introducing him as "Smilin' Jack". Inevitably, a record contract followed and Jack enjoyed a string of hits on the Capitol label, all of which are included here. When television started to take over, Jack became a game show host on television that paved the way for his long-running role as host of the incredibly successful TV show You Asked For It, which lasted until 1991. It is the happy songs collected here on CD for the first time that were his most successful and which indisputably prove the reason he was dubbed "Smilin' Jack" all those years ago.