- Until 2000, Bob Benny played in musicals. In Flanders, his most famous role is that of Doolittle in My Fair Lady.
- In 1963, Benny scored his biggest hit, (Waar en Wanneeer) 'Where and when', an adaptation of 'Als Flotter Geist' composed by Johan Strauss. He won a gold record with it.
- In the early fifties he started working for public broadcasting, where he had several shows of his own, with a lot of singing and dancing.
- Benny began his singing career at the end of World War II when he started performing regularly at a café in Sint-Niklaas.
- He was a Belgian singer and musical theatre performer,.
- In 1951 Benny auditioned for the Flemish Broadcast NIR and was subsequently allowed to perform in the radio program De antenne Zingt.
- By the early 1950s, he had regular spots on radio and released his first album 'Mijn hart spreekt tot u '(My Heart Speaks to You).
- His fame from the Eurovision song contest got him performances in several European countries.
- Bob Benny chose his stage name when he was singing after World War II with the Metro Club Orchestra. The leader of that orchestra was called Robert and he derived the name Bob from that. He played clarinet in the style of Benny Goodman, so he chose Benny as his last name.
- In 1961, Benny was again selected to represent Belgium, with the song "September, gouden roos" ("September, Golden Rose"), in the sixth Eurovision, which again was held in Cannes, on 18 March. Although the contest had now expanded to 16 participants, "September, gouden roos" only managed to pick up one point from Luxembourg, consigning Benny to a joint last-place finish with Austria's Jimmy Makulis.
- In 2006, Benny celebrated his 80th birthday and claimed he was back to full health.
- In 1959 Bob Benny represented Belgium at the Eurovision Song Contest in Cannes. He shared the sixth place with his song 'Hou Toch van Mij', the Flemish entry that achieved the highest place ever at the Eurovision Song Contest. It wasn't until 2010 that Tom Dice was able to match this.
- Bob Benny participated in the Eurovision Song Contests of 1959 and 1961. In 1959, Benny was chosen, with the song "Hou toch van mij" ("Do Love Me"), as the Belgian representative in the fourth Eurovision Song Contest which took place on 11 March in Cannes, France. Hou toch van mij received votes from five of the other 10 participating countries and finished in sixth place.
- In 2002 he was inducted into the Flemish Radio 2 Hall of Fame for a lifetime of music.
- In 2001, Benny suffered a stroke and fell into financial difficulties. A benefit concert on his behalf took place in Antwerp in April 2003, featuring the music of Richard Rodgers performed by well-known Flemish artists.
- He performed in Berlin for six years in the musical "Mein Freund Bunburry" and the operetta "Maske in Blau".
- On 29 March 2011 the Flemish broadcaster Vlaamse Radio- en Televisieomroep (VRT) reported that Benny had died in a nursing home in Sint-Niklaas. (Flanders).
- In 1957, he had his first hit single with "Cindy, Oh Cindy", which reached No. 2 on the Belgian chart.
- He has also worked for years as entertainer on cruise ships.
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