Paul McGann was originally cast as Sharpe. Two weeks into filming he ruptured a cruciate ligament playing football during a break, but attempted to keep going as the ailment was misdiagnosed. However, the injury was aggravated while shooting a fight scene and again during a rock-climbing scene, to the point where McGann had no choice but to drop out. When Sean Bean was cast, the majority of the season had to be reshot. A planned third episode based on Sharpe's Gold was dropped as the delays cost them too much time.
Sean Bean (Richard Sharpe) and Daragh O'Malley (Patrick Harper) are the only actors to appear in all 16 episodes of the series.
In his memoir, Brian Cox speaks at length about the grueling production of the first season. The English crew was filming in the Crimea, dangerously close to the former Chernobyl nuclear power plant, with Russian co-producers who took every opportunity to cut costs and a director who was constantly drunk or hungover. Nearly the entire cast and crew were taken ill by giardia, a water-based parasite that causes severe stomach cramps and diarrhea and was remedied with enemas to flush it out. The animals were regularly abused, including the use of tripwires to make horses fall. This lax approach to safety included the actors; while filming a battle scene for Sharpe's Eagle an extra was accidentally stabbed, the footage of which was reportedly used in the final cut. The shutdown that occurred after Paul McGann was forced to drop out included the director being replaced and new stunt coordinators being hired. Despite this, the rest of the shoot was just as miserable, which led to Cox's vow never to reprise the role.
Richard Sharpe is notable for being one of the few characters Sean Bean has played who does not die.
In his book chronicling the making of the series, Jason Salkey (Rifleman Harris) claims that his and the other supporting actors' relationship with director Tom Clegg was often strained and even combative. Clegg, who was under enormous pressure to maintain a very tight schedule, showed little interest in developing the Chosen Men as characters or even giving them much screen time. At a wrap party for the third series, an intoxicated Clegg reportedly admitted that he would not have cast Salkey or many of the other actors had he been involved in those decisions. Daragh O'Malley took it upon himself to advocate for the cast whenever he could, especially in light of the miserable filming conditions, which allegedly led to at least one attempt to fire him.