His father, John Shakespeare, was a glover living in Henley Street, Stratford, and an alderman of the town from 1564. Gilbert may have been named after Gilbert Bradley, also a glover, who lived on the same street and who in 1565 was one of the capital burgesses of Stratford.
In London, Gilbert Shakespeare was a haberdasher, a seller of needlework supplies such as thread, needles, and ribbons, living in the parish of St Bride's. In 1597 he and a shoemaker stood surety for £19 bail for William Sampson, a Stratford clockmaker, in the Court of Queen's Bench.
Gilbert Shakespeare seems to have moved back to Stratford by 1602. On 1 May of that year he acted as his brother William's agent in taking delivery of the deed to 107 acres of farm land in Old Stratford, which William Shakespeare had bought from John and William Combe for £320. Along with several unsavoury Warwickshire characters, Gilbert was named in a bill of complaint on 21 November 1609 instigated by Joan Bromley, a Stratford widow, but the details of the suit are unknown. He signed his name in a neat Italian hand, "Gilbert Shakesper", as witness on 5 March 1610 to a lease of property in Bridge Street in Stratford.
The register of the Holy Trinity church records the burial of "Gilbert Shakspeare, adolescens" on 3 February 1611/12, which today is generally taken to be the Gilbert Shakespeare baptised in 1566. Charlotte Stopes tracked every usage of the terms adolescens, adolocentulus and adolocentula and their variants in the Stratford parish register and came to the conclusion that adolescens meant only that Gilbert Shakespeare died unmarried, especially in the absence of any records of his marriage, the baptism of his child, any other record of his death, and the fact that he is not mentioned in his brother's will. Mark Eccles and Schoenbaum have followed her judgement.
Earlier biographers, however, speculated that this might be his son instead. Of the burial entry, Sidney Lee wrote: "'Gilbert Shakespeare adolescens,' who was buried at Stratford on February 3, 1611-12, was doubtless son of the poet's next brother, Gilbert; the latter, having nearly completed his forty-sixth year, could scarcely be described as adolescens; his death is not recorded, but according to Oldys he survived to a patriarchal age." Oldys wrote in the mid-18th century, without certainty as to identity: "One of Shakespeare's younger brothers, who lived to a good old age, even some years, as I compute, after the restoration of King Charles the Second... The curiosity at this time of the most noted actors to learn something from him of his brother, etc., they justly held him in the highest veneration..."
- Schoenbaum, S. (1977) William Shakespeare: A Compact Documentary Life. Oxford: Oxford UP, ISBN 0-19-502433-8, pp. 26-7; Honan, Park. (1998), Shakespeare: A Life, Oxford: Oxford UP, p. 23.
- Schoenbaum p. 27.
- Honan pp. 229-30.
- Schoenbaum, p. 27.
- C. Stopes, Shakespeare's Environment (1914), London, pp. 333-5.
- Eccles, Mark Shakespeare in Warwickshire (1961), Madison: University of Wisconsin Press, p. 108; Schoenbaum, p. 27.
- Skottowe, Augustine. The life of Shakespeare (1824), London, I:7.
- Lee, Sir Sidney. Shakespeare's life and work: being an abridgement, chiefly for the use of students, of A life of William Shakespeare, (1900) London, p. 151; Lee, Sir Sidney. "William Shakespeare" Dictionary of National Biography, (1897) London, 51:393.
- Yoell, James, ed. Memoir of William Oldys, Esq. (1862) London, pp. 45-46.