Herbert "Jessie" James was a childhood friend of Albert Tatlock and Minnie Caldwell who went on to become headmaster at Alf Roberts's school.
Born in 1896, Herbert knew Albert as far back as Bessie Street infants, where Albert once thumped his earhole. At school, Herbert gave Albert the nickname 'peewee', much to the ire of his short-legged friend. Albert came to resent over-achiever Herbert and longed to best him; the pair arranged a swimming race only for Albert to drop out, claiming to have pulled a muscle. In 1973, Ena Sharples revealed to Herbert that the true reason for Albert not racing was that his mother had threatened to leather him. Even Albert's proudest moment produced feelings of inadequacy in the man as when the local men returned from the First World War in 1918, Herbert was the one who got his picture in the Gazette, due to his uncle being the paper's editor.
In April 1973, with a long career in teaching behind him, and a marriage which produced at least one daughter, Herbert paid a visit to the Rovers to congratulate his old pupil Alf on being appointed Mayor of Weatherfield and wish him a successful year in office. While in the area, he visited Albert at 1 Coronation Street. When he saw that his friend was looking his age, Herbert told him about his passion for exercise - particularly walking - and encouraged Albert to go on a trip into the country with him. Although bored by Herbert's boasting, Albert felt compelled to prove himself just as capable as Herbert and decided to walk the Pennine Way, which Herbert did yearly. Albert's lofty ambition concerned Ken Barlow, who asked Herbert to talk his uncle out of it, but Herbert - not knowing just how stubborn Albert could be - felt confident that Albert would either forget the idea or give up after four miles.
Embarking on the walk with Jerry Booth, Albert amazed his friends and neighbours by apparently completing it - neglecting to tell them that they had skipped a chunk of their route by hitching a lift. When Albert went to Herbert's house to brag, his daughter informed him of the sad news that Herbert had died of a heart attack the previous Friday.
- The character was credited as "Herbert 'Jessie' James".