In 1959, Como moved to Wednesday nights, hosting Perry Como's Kraft Music Hall weekly for the next four years. Over the next four seasons, from 1963 to 1967, the series was presented as monthly specials alternating with Kraft Suspense Theatre, The Andy Williams Show, and finally The Road West. Como became the highest-paid performer in the history of television to that date, earning mention in the Guinness Book of World Records. Como himself took part in none of this; his production company, Roncom, named for son Ronnie Como, handled the transaction along with all other Como business matters. Como also had control of the show which would replace his during the summer television hiatus. While "Mr. C." was having a holiday, viewers would see Perry Presents, beginning in 1959.  In late 1962, after the Cuban Missile Crisis had settled well enough to permit the evacuated servicemen's families to return to Guantanamo Bay Naval Base in Cuba, Secretary of Defense Robert McNamara was eager to do more for morale there. He asked Perry Como to bring his television show to the Naval base. Perry and his cast and crew were at Guantanamo when the loved ones began their return. The first entertainers to visit the base since the crisis, the Como show filmed there for eight days. Some highlights of the program, which was seen in the US on December 12, 1962, included Como's shaving a serviceman with a Castro-like beard and the enthusiastic participation when Perry asked for volunteers to come on stage to do the Twist with the lovely ladies who were part of the visiting dance troupe.  Filming for the Kraft Music Hall Christmas show that was aired on December 17, 1964 began at the Vatican November 7. By special permission of Pope Paul VI, Como and his crew were able to shoot segments in the Vatican gardens and other areas where cameras had never been permitted previously. The show featured the first television appearance of the Sistine Chapel Choir, and also the first time a non-choir member (Como) sang with them. The choir performed a Christmas hymn in Latin written by their director, Domenico Bartolucci, called "Christ Is Born", as part of their presentation. Como asked his associate, Ray Charles, to write English lyrics for the song, using it many times on both television shows and his Christmas albums. The Carpenters also recorded the song on their first Christmas album, Christmas Portrait.

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