The documented history of the site of the original Bear Inn on the High Street has been traced to 1241, when Lady Christina Pady bequeathed the property to St Frideswide's Priory in return for having a private mass said for her for eternity; at that time it had a dwelling house, later called Parn Hall, but this burned down in 1421.

It was known as The Bear Inn by 1457, and by 1523 the land at the rear was part of the pub's property; it contained stables for the coaching horses, and was bounded to the south by St Edward's churchyard.

During the Dissolution of the monasteries between 1536 and 1541 the priory was taken over by Thomas Wolsey, who created Christ Church on the grounds, and the "eternal" masses for Christina Pady ceased.

[14] Wolsey closed down the priory (ending Christina Pady's perpetual masses), and built Cardinal College (now Christ Church) on the grounds.

[15] Following Wolsey's fall from grace in 1539, the land was taken over by Henry VIII, who, in 1545, sold parts of the property, including 123 and 124 High Street, to one of his courtiers Richard Taverner and his younger brother Roger.

[2] When The Bear Inn's premises on the High Street were rebuilt and converted into private housing in 1801, its business name transferred to the Jolly Trooper.

[3] A distinctive feature of the Bear is a collection of over 4,500 snippets of club ties, started in 1952 by the landlord, Alan Course,[2] who had worked as a cartoonist at the Oxford Mail.

[26] In Robert Boris's 1984 comedy movie Oxford Blues, The Bear is where the main character, Nick Di Angelo, and his student friends occasionally meet to drink.

[28] Oxford-educated Australian arts leader Anthony Steel recalls in his autobiography, Painful in Daily Doses: An Anecdotal Memoir, that Alan Course, the landlord, played the Last Post on his bugle, for a student lying in the middle of the street outside the pub.