Born to a theatrical family, Robertson began as an actor, but he was not a success and gave up acting in his late 20s. After earning a modest living writing articles for the press, translating and adapting foreign plays and writing several of his own plays he achieved success in 1865 with his play "Society", which the actor-manager Marie Wilton presented at a small London theatre, the Prince of Wales's. Over the next five years Robertson wrote five more plays for the Prince of Wales's. Their naturalistic style and treatment of contemporary social issues was in strong contrast to the melodramas and exaggerated theatricality to which the public had been accustomed, and Robertson's plays were box-office and critical successes. Robertson supervised their productions and was a pioneer of modern stage directing.