In 1778 he became professed as an Augustinian, but due to his turbulent character he spent a great part of his time in prison and was constantly being transferred from one convent to another, which resulted in him leaving the monastic lifestyle in order to live in urban Lisbon.

His made an attempt to supersede Luís de Camões as Portugal's greatest poet, and in 1814 he produced Oriente, an epic dealing with the same subject as the Os Lusíadas, namely Vasco da Gama's discovery of the sea route to India.

[1] Macedo founded and wrote for a large number of journals, and the tone and temper of these and his political pamphlets induced his leading biographer to name him the chief libeller of Portugal, though at the time his jocular and satirical style gained him popular favor.

His malignity reached its height in a satirical poem in six cantos, Os Burros (1812–1814), in which he pilloried by name men and women of all grades of society, living and dead, with the utmost licence of expression.

His translation of the Odes of Horace, and his dramatic attempts, are only of value as evidence of the extraordinary versatility of the man, but his treatise, if his it be, A Demonstration of the Existence of God, at least proves his possession of very high mental powers.