[2] His father's influence saw him made fellow of Trinity in 1728; but he never settled to a career, endured financial troubles, and spent time in France and Jersey.
[3] During the 1750s Bentley developed significant friendships, with Horace Walpole and Thomas Gray;[3] in Jersey in 1754 he met also Johann Heinrich Müntz.
[10][11] The poem illustrations have been thought connected with the style of Jean Bérain; Bentley's subsequent architectural designs were eclectic.
His comedy The Wishes, or Harlequin's Mouth opened was acted at Drury Lane for three nights (27, 28, 80 July 1761), and at Covent Garden, 3 October 1761.
His tragedy Philodamus (printed 1767), with its scenes of courtship, paternal vigilance, and spousal preparations, is said to have convulsed the house with laughter.