Healy first received attention as a performer of his own "songs of social significance" during the 1960s. Later he wrote comedy songs for Billy Connolly, including "The Orient Express-a tale of intrigue and cross dressing", "The Shitkickers Waltz", and "The Country &amp; Western Supersong". Healy achieved his greatest success as a songwriter with "What's Another Year", which won the 1980 Eurovision Song Contest. Over the course of the next 15 years, the song earned him a total of £250,000. In 1983 his song, "Edge Of The Universe", sung by Linda Martin, was the overall winner of the Castlebar Song Contest. Under the name of Crack, he and Dave Pennefather released a parody song called "Silly Fellow", which was about Paul McCartney's arrest and jail experience in Japan. Healy and Pennefather also released a parody of Abba's song "Mamma Mia" that they called "Hey C'mere" and credited to Rubbish.