As a young man, he was educated at Waterford Grammar School and later went to Trinity College, Dublin[1] where he took no degree, but was awarded the Vice-Chancellor's Medal for his poem "Poland."

He had some success, despite limited artistic training, but his disorderly lifestyle and reputation for missing appointments undermined his career.

[3] He found his true vein in drama, and produced over 30 plays, after having his first major success with The Man of Airlie (1867), which was shown in London and New York.

Some of his most notable works there were Medea in Corinth, Eugene Aram, Jane Shore, Buckingham, and Olivia, a dramatisation of The Vicar of Wakefield, which had great success.

Harold Child in The Cambridge History of English and American Literature commented, His caricature of Oliver Cromwell in Charles I (1872) must strike anyone who has seen or read that play not only as ridiculous, but as a sacrifice of dramatic for theatrical effect; and, to judge from contemporary criticism, his treatment of John Knox in the unpublished Marie Stuart (1874) was no better.

In 1880 he created a revised version of Henrik Hertz's play King René's Daughter under the title Iolanthe.

[1] He wrote several novels after The Wife's Evidence, including Notice to Quit (1863) and The Love That Kills (1867), both of which deal with the aftermath of the Great Famine of Ireland.

Wills' long blank verse narrative poem Melchior, in the manner of Browning, was strongly recommended by Oscar Wilde.

Richard Cordell described Broken Spells as "a flatulent Napoleonic piece", adding that Wills "wavered between uninspired verse plays and noisy melodrama".