With renewed confidence, Henshall returned to London and in 1993 landed the pivotal role of an abusive English army officer in the Dennis Potter-scripted TV-movie "Lipstick on Your Collar" (Channel 4). So successful was his performance (which earned critical raves), the actor became typecast. "I just got offered variations on the same role, which I didn't want to do." Instead, he returned to stage work, this time with the Royal Shakespeare Company. "Angels and Insects" (1995) offered the opportunity to play a sarcastic aristocrat (with an unhealthy attachment to his sister) which proved more popular on the American art-house circuit than in England. He was virtually wasted, though, in the subpar fantasy adventure "Kull the Conqueror" (1997). On the other hand, "Fast Food" (1998), while uneven, proved he could be a strong romantic lead given the right material.
After a well-received stage performance in David Mamet's "American Buffalo" in 1997, Henshall was approached by former co-star Peter Mullan with an offer to co-star in Mullan's feature directorial debut "Orphans" (1998). Playing one of four siblings coping with the recent death of their mother, the actor offered a nuanced turn that skillfully negotiated the script's comic and tragic moments. His Michael spend the evening of his mother's funeral loping through the streets of Glasgow after being stabbed in a pub fight before finally coming to a realization by the Clyde River. Henshall has been very forthcoming in interviews over the struggle he had in interpreting this character as it required him to call upon his own mother's death. Perhaps in response to having to plumb those dark memories, he segued to back-to-back romantic comedies. In "If Only/Twice Upon a Yesterday" (1998), Henshall proved winning as an unemployed actor who finds he has a chance to replay a pivotal moment in his life. "This Year's Love" (1999), a sexual roundelay involving three couples who swap partners inadvertently over a three-year period, again allowed the actor to display his charm and charismatic screen presence. As if to avoid being pigeonholed in romantic leads, Henshall displayed his astonishing range by undertaking the starring role in the Channel Four series "Psychos" (1999), playing a highly competent but foul-mouthed and lecherous psychiatrist.