He was born near L'Ancresse, Vale, Guernsey and began his career as an assistant professional at the Royal Guernsey Golf Club which was founded in 1890. He fought in the First World War and was then club professional at Foxgrove Golf Club, Hendon, Benton Park and then at Branshaw Golf Club in West Yorkshire. In the 1923 Yorkshire Evening News Tournament, Jolly only qualified for last-32 knock-out stage by winning a five-man, 18-hole playoff for the final place. After winning his first round match comfortably, he only beat Abe Mitchell at the seventh extra hole after Mitchell had missed from 2 feet at the third extra hole. Jolly holed a 9 footer at the 7th, despite being "partially stymied". In the third round, he beat Gus Faulkner at the second extra hole before a 2 and 1 semi-final win. In the final against Walter Hagen, the match went to the 36th hole, Jolly winning by 2 holes. Jolly had been 4 up after 7 holes of the afternoon round but Hagen levelled the match at the 13th. Jolly won the 17th after Hagen was bunkered and then won the last after Hagen three putted. Jolly was not initially selected for the nine-man 1927 Ryder Cup team that was announced in early March. In May, the health of Abe Mitchell, the British captain, gave some concern and it was eventually decided that he was unfit to travel. Later he was operated on for appendicitis. Seven members of the team left on the Aquitania on 21 May, Aubrey Boomer being picked up in Cherbourg. With the team a man short, the PGA Secretary Percy Perrins recruited Jolly who sailed on a later boat, the Majestic, and arrived in New York on 31 May, four days after the rest of the team. The Ryder Cup was played in Worcester, Massachusetts on 3 and 4 June. Jolly played in both the foursomes and the singles, losing both his matches. Jolly continued to have considerable successive in the Yorkshire Evening News Tournament. He lost three successive finals in 1927, 1928 and 1929 before winning for the second time in 1930, beating Owen Sanderson 3 and 1 in the final. The match was played on the same day as the 1930 Amateur Championship final in which Bobby Jones beat Roger Wethered. Jolly won the Roehampton Invitation Tournament in April 1931 and, in early May, after a series of trial matches using the new American-sized ball, he was selected as one of an initial six players in the British 1931 Ryder Cup team. The team was finalised after the Open Championship in early June. As well as announcing the final member of the team it was also reported that Jolly had withdrawn because of a lack of form and had been replaced by Arthur Havers. Jolly had failed to qualify for the Open Championship after scoring 84 and 78 in the qualifying rounds, the only occasion between 1926 and 1936 that he failed to qualify, He died in Clayton, Bradford, West Yorkshire.