Born in Blandford Forum, Dorset, England, Bastard is best known for seven books of 285 epigrams entitled Chrestoleros published in 1598.
Subsequently he began studying at New College, Oxford, on 27 August 1586.
Though later expelled from his Fellowship, Bastard still received a BA in 1590, and an MA 16 years later in 1606.
He still maintained a few supporters and admirers, primarily, Sir Charles Blount, Lord Mountjoy who appointed him as a chaplain, and Thomas Howard, 1st Earl of Suffolk who appointed him vicar of Bere Regis and later, in 1606, Rector of Almer in Dorset.
Prior to Bastard's death, admirer Sir John Harrington said in a poem: