In the first TMNT movie, Leonardo was fairly modest and sensitive, rarely issuing direct commands and seemingly much more relaxed around his brothers thinking of himself as more of an equal than a leader; he also joked around with his brothers much more than in other versions of the TMNT. Since the film was mostly based on the Mirage comics, one can best compare Leonardo's personality with his counterpart from the comics. He is rather quiet, always trying to put together a plan before he attacks and is again the one that is closest to Splinter. It was he who first communicated telepathically with a kidnapped Splinter in the first movie. In this version he clashes more often with Raphael, as they are just too different. Though they are basically still close as brothers. While he was not ambushed by the Foot Clan (Raphael was) he seems the most anxious about Raphael's health after his ambush by the Foot Clan. When Raphael was seriously injured Leonardo kept guard by his side day and night. He also did not kill the Shredder. However he fought alongside his brothers against The Shredder in the climactic battle, and he is the only one of the four Turtles to successfully injure the Shredder during their climactic battle, but, like his brothers, could not defeat him. Due to the focus on Raphael in the film's plot, Leonardo's personality was rarely explored and his leader position in the team took a back seat. He was portrayed by David Forman and voiced by Brian Tochi.
In Teenage Mutant Ninja Turtles II: The Secret of the Ooze, Leonardo was much more prominent and his leader position was brought to focus. He is seen on many occasions bickering with Raphael as their sibling rivalry begins to become much more serious. He, like his brothers, was astonished at the return of the Foot but he found that their current homelessness due to their last battle was a more pressing issue and soon he convinced his brothers that they needed to move. Leonardo is once again sensitive, caring, and humorous in this adaptation but he now displays far more aggressive leadership tendencies.
In Teenage Mutant Ninja Turtles III, Leonardo helps his brothers back in feudal Japan to go back home after helping a village in trouble from the greedy-western-colony driven man, Walker. Leonardo at this point in the movie series had become less and less of a leader, shouting out wise cracks and goofing off with his brothers, a flaw not present in other incarnations of Leonardo. He was the one who defeated Lord Norigana by trapping him within a Japanese Bell before cutting his pony tail off mocking him about a new haircut. Like his brothers minus Donatello, he seemed at home in ancient Japan. In this flim there wasn't much for him to really do, he was just portrayed as a goofball making only a few smart decisions.
In both Teenage Mutant Ninja Turtles II: The Secret of the Ooze and Teenage Mutant Ninja Turtles III, his actor was Mark Caso and he was voiced again by Brian Tochi.