Hugh Jackman's early film career showcased his versatility beyond action roles, with 'Kate & Leopold' serving as a key opportunity to demonstrate charm and romantic appeal in a period fantasy setting. The role required him to master various period-appropriate skills, including horseback riding, though the behind-the-scenes reality proved far less graceful than it appeared on screen.

During production of a riding scene, Jackman revealed that after initially claiming to be learning to ride, his horse unexpectedly halted mid-shot, causing him to fly over the animal's neck and land hard on the ground. He characterised the moment as deeply embarrassing and painful, though his co-star's willingness to continue filming with him afterwards earned his admiration.