Born in Galston, Ayrshire, inside right Jimmy Howie played for local junior side Galston Athletic in 1897 before he joined Kilmarnock in 1898, making his Scottish League debut against Airdrieonians that August, scoring in a 5-0 victory. He was in the side that won the 1899 Scottish Second Division title and the following season earned selection to The Scottish League, playing against The Irish League in Belfast in February 1901. After scoring 28 goals in 61 matches for Killie, he joined Southern League club Kettering Town later in 1901 then moved to Bristol Rovers the following season, where he scored 10 goals in 26 appearances during their 1902-03 campaign.
Howie was signed by First Division club Newcastle United in May 1903, making his Football League debut against Aston Villa the same September, and between then and 1910 he made 237 appearances for the club over the next seven seasons, scoring 82 goals. He won the Football League Championship three times (1904-05, 1906-07 and 1908-09) and was also an FA Cup winner in 1910, as well as a losing finalist in 1905, 1906 and 1908. In his second season for Newcastle he scored a career best 18 goals including all three goals in a 3-1 win at Wolverhampton Wanderers in November 1904, and was the club’s leading goalscorer.
During this period he earned three caps for the Scotland, making his international debut in a 1-0 defeat to England at The Crystal Palace in April 1905. His other 2 caps were also against England, in April 1906 he scored twice in a 2-1 win at Hampden Park, and in April 1908 he played in a 1-1 draw at the same venue.
Howie was universally known in the game as “Gentleman James” but was equally notable for his peculiar running action, which looked like a hopping motion. After losing his place at the start of the 1910-11 season, playing a final 3 matches for The Toon in November, he left Newcastle in December 1910, signing for newly elected Second Division club Huddersfield Town, where he spent three seasons scoring 18 goals in 87 appearances before retiring.
In 1913 Howie moved into management when appointed manager of Queens Park Rangers, a position he held for seven years. He was then secretary-manager of Middlesbrough from March 1920 until May 1924.
His younger brother David, also a sucessful professional footballer, playing for Kilmarnock and Bradford Park Avenue.