By 1682 he was greatly influenced by John Dryden and produced his first play, The Loyal Brother, which was performed at the Theatre Royal, Drury Lane by the King's Company.

Southerne bought his prologue and epilogue from Dryden, who made extra income from his ability to turn such pieces.

[2] By 1688, "his subject once again ends up in a novel by his colleague Aphra Behn,Oroonoko, or The Royal Slave was performed as a play and was a huge success".

According to Kaufman, "At the age of sixty-seven Southerne offers one last play, Money The Mistress in 1726, it is a weak conclusion to an honorable career."

Today readers are interested in his psychological realism, his portraits of complex characters, often women in the throes of domestic distress, and his coldly realistic, often harsh, analysis of corrupt societal relations".

One of the major changes that Southerne made to his play from Behn's version was that he turned Imoinda's skin color from black to white.

[4] Southerne plays with the idea of a double plot: one path that deals with the tragic fates of the newly interracial African lovers and the other on Charlotte's comical take on finding rich husbands for herself and her sister.

Tachmas, the loyal brother, is obviously a flattering portrait of James II, and the villain Ismael is generally taken to represent Shaftesbury.

In 1692 he revised and completed Cleomenes for John Dryden; and two years later he scored a great success in the sentimental drama of The Fatal Marriage, or the Innocent Adultery (1694).

Living in this relatively new world without her husband, Isabella finds herself raped and taken of her innocence by an admirable man in the play who goes by Villeroy.

According to the Encyclopædia Britannica Eleventh Edition, "[t]he general spirit of his comedies is well exemplified by a line from Sir Anthony Love (1691) "every day a new mistress and a new quarrel."

As so, the message is clear in the play as it is for that time period, women who were sinful and simply not pure were not worthy of marriage and a happy life.

[9] Southerne's later pieces did not achieve any great successes, but he contrived to gain better returns from his plays than Dryden did, and he remained a favourite with his contemporaries and with the next literary generation.

[8] His other plays were: The Disappointment, or the Mother in Fashion (1684), founded in part on the Curioso Imperlinente in Don Quixote; The Wives Excuse (1691), or Cuckolds make themselves (1692); The Maids Last Prayer; or Any rather than fail (1692); The Fate of Capua (1700); The Spartan Dame (1719), taken from Plutarch's Life of Aegis; and Money the Mistress (1726).

[8] A Compendium of Irish Biography (1878) described him as: "frugal and pushing; he was peculiarly fortunate in the sale of his plays; and his judicious flattery of the Duke of York considerably advanced his interests.

Two of his plays, all that are now known to the public, are thus commented on by Hallam: "Southern's Discovery, latterly represented under the name of Isabella, is almost as familiar to the lovers of our theater as Venice Preserved itself; and for the same reason, that whenever an actress of great tragic powers arises, the part of 'Isabella' is as fitted to exhibit them as that of 'Belvidera.'

The choice and conduct of the story are, however, Southern's chief merits; for there is little vigour in the language, though it is natural and free from the usual faults of his age.

A similar character may be given to his other tragedy, Oroonoko, in which Southern deserves the praise of having first of any English writer, denounced the traffic in slaves and the cruelties of their West Indian bondage.