In Toy Story, Lenny was one of the first toys to come out into the open room when Woody signaled that the coast was clear. Lenny also appears at the staff meeting before Andy's birthday party in shock that his party was moved to that day, even though Andy's birthday was not until the following week. When Hamm alerts the toys that the birthday guests have arrived, Lenny, along with basically every other toy, except Woody, runs to the window to see what kind of sized presents his friends are bringing, in fear that Andy may get bigger toys and that they will all be given away. Lenny, in particular, showed great fear when Sarge and his army reported what presents Andy was receiving.
One of Andy's presents turns out to be a toy named Buzz Lightyear. Lenny, just like the rest of the toys, takes an immediate liking towards him. One afternoon, when the toys hear Sid in his backyard, Buzz uses Lenny to watch him and his dog Scud mess around with one of his army toys. Lenny warns the toys when he sees Sid light up the fuse on the Combat Carl toy just before it explodes. On that same night, Woody accidentally knocks Buzz out the window. While most of the toys believe that Woody did this intentionally, Lenny is one of the few that do not accuse him of doing this on purpose. However, he loses his trust in him when he sees Woody holding Buzz's severed arm when Woody is trapped in Sid's house.
Andy's family soon moves out of their house and the toys are placed inside moving trucks. when Woody attempts to save Buzz with RC Car, Lenny attacks him, along with all the others, thinking that Woody was trying to "murder" RC by kicking him out of the moving van. The toys then proceed in tossing Woody out the back of the truck as well. While the other toys celebrate, Lenny alerts the toys that he sees Woody riding on RC with Buzz and approaching the truck. Bo Peep uses him to get a closer look and informs everyone that Woody was telling the truth, making the other toys realize that they made a terrible mistake. Lenny alerts the toys again when RC, Woody, and Buzz approach the truck fast by Sid's rocket taped to Buzz's back, just before Buzz and Woody drop RC back into the moving van. Lenny appears again at the end of the film in Andy's room at the Christmas present meeting, appearing alongside Slinky, Robot, and Troikas before hearing what presents Andy receives for Christmas.
Lenny appears with a non-speaking role in the sequel. He first appears at the beginning of the film helping Hamm look for Woody's hat. When the Davises have their yard sale, Lenny, along with the rest toys panic in fear that they will be sold. After Woody heads down to the yard sale with Buster to help save Wheezy, Woody gets thrown off Buster and gets stuck outside. Buzz uses Lenny to keep watch on Woody during these events at the yard sale until Al McWhiggin of Al's Toy Barn steals Woody, prompting Lenny and the other toys to panic. Lenny appeared one more time at the end of the film when the toys reunite and listen to Wheezy sing "You've Got a Friend in Me", using Mr. Mike as a karaoke machine.
Lenny makes a brief cameo at the start of Toy Story 3, in a series of home videos taken by Andy's mother. It was revealed by Woody that he was sold at a yard sale over the time span between the second and third film, along with Wheezy, Etch A Sketch, Bo Peep and many other toys.
- Lenny speaks in Toy Story by moving his eyes around.
- Lenny's name comes from a play on the word "lens."
- Lenny only speaks in Toy Story; in subsequent material he is silent.
- In an outtake of Toy Story 2, he is seen being used by Buzz and the binocular-marker trick is pulled by Woody.
- Lenny is based on the "Roving Eyes" windup toys released in 1982 from TOMY.
- The TOMY "Roving Eyes" wind up toys were also featured in the 1984 Disney film, Where The Toys Come From.
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