He was, according to Wisden, "so highly ... regarded" that he was selected three times for the Gentlemen v Players fixture before he had played a match during the season. In 1924 he took leave of absence from his teaching post to travel with the England team to Australia over the 2014–15 English winter. He played in the non-first-class match in Ceylon and in first-class matches against Australian State cricket sides and an Australian XI but could not break into the Test side. Bryan was well-regarded as an opening batsman. His Wisden obituary calls him a "a model opening bat" who aimed to "lay a good foundation to the innings" before attacking It regarded him as a "potentially great" cricketer who was a "beautiful field(er)" and "bowled slow leg-breaks and googlies" He scored over 8,700 runs in first-class cricket including 17 centuries. His highest score was 236 runs made against Hampshire in 1923 at Canterbury, an innings Wisden singled out as an example of his approach to batting. He played 119 times for Kent and 11 times for Cambridge as well as making appearances for teams such as the Gentlemen and, eight times, MCC. He played his final match for Kent in August 1932 against Middlesex at Lord's before playing one more first-class match in 1933 for H. D. G. Leveson Gower's XI against Cambridge University at Eastbourne. He continued to play club cricket until the 1950s for Eastbourne and coached cricket in his teaching post. Bryan worked as a school teacher at his old school, St Andrew's, in Eastbourne from 1922. He married Irene Pocock in March 1927 and together they had one son. He was Master-in-Charge of cricket at the school and was, for a term, Headmaster before having to step down due to his wife's ill-health. He continued to be associated with the school after his retirement. Two of his brothers, Ronnie and Godfrey, also played first-class cricket for Kent. All three played in just one match together for the county, against Lancashire at Dover in August 1925, with Jack captaining the Kent side. Ronnie shared the Kent captaincy with Bryan Valentine in 1937. Bryan died after a short illness at Eastbourne in 1985 aged 88, at the time the oldest living Kent player and the last survivor of the Cambridge side of 1922 and the England touring side of 1924/25.