Trinidadian calypsonian Roaring Lion recorded "Ugly Woman" in 1934, during his first trip to New York. It immediately became popular, and Lion continued to record it throughout his career. The calypso offers advice on finding a faithful spouse: "From a logical point of view / Better marry a woman uglier than you." Other calypsonians responded to Lion: Lord Beginner extolled feminine qualities in "Pretty Woman," while Frank Holder, based in England, wrote "Nice Woman."
"Ugly Woman" became the first calypso to be performed in a movie, when Sir Lancelot sang it in the Hollywood musical Happy Go Lucky (1943). New York-based calypso singers the Duke of Iron and MacBeth the Great further popularized the song during the 1940s. In the early 1950s, the Mighty Charmer (later known as Louis Farrakhan) recorded it, while the pianist Liberace performed it on his television show. Hollywood actor Robert Mitchum included it on his 1957 calypso album. In 1963 the calypso (under the title of "If You Wanna Be Happy") became a number one rhythm and blues hit by Jimmy Soul. Soul's version was written by record producer Frank Guida, who had been stationed in Trinidad during World War II.
During the late1940s/early 1950s, choral director Leonard De Paur recorded "Ugly Woman" with his Infantry Chorus. He later published an arrangement of the song under the title "Marry A Woman Uglier Than You." This arrangement made the song a favorite with choral groups around the world, and it remains a choral standard to this day. The Southern California Vocal Association, for example, lists it as a recommended song for festival competitions.
