Skipper Riley is the deuteragonist of Planes and a supporting character in Planes: Fire & Rescue. He was a World War 2 Vought F4U Corsair who served the American navy onboard the USS Dwight D. Flysenhower, better known as the Jolly Wrenches. He is voiced by Stacy Keach.
Skipper is a grey plane who lives in Propwash Junction, a whole town full of airplanes. He runs Skipper's Flight School with his assistant Sparky, and he teaches Mater how to fly in Air Mater. Skipper learns that he can really teach anyone how to fly, guaranteed. He watches as Mater flies in the sky. Later, he and Sparky attend the air show, in which Mater was recruited as a Falcon Hawk. Sparky pointed out Skipper as Mater's mentor to Mia and Tia, impressing them.
Skipper appears to be a little judgmental in Planes, as he hesitated to teach Dusty how to fly well at first. After Dusty passed qualifying, however, Skipper then realized he had been a little harsh and agreed to help Dusty and his friends.
Planes: Fire and rescue
As Dusty becomes a world-renowned racer, Skipper attends one of his races with his friends, and later watched Dusty's interview with Brent Mustangburger, in which Dusty gives credit to his supportive friends. Later, after Dusty wins the Red Bulldozer race and returns to Propwash Junction for the annual Corn Festival, Skipper takes his protege out for a practice flight. Suddenly, mid-flight, Dusty's prop stall and starts falling uncontrollably out of the sky before restarting his engine, forcing the pair to make an emergency landing. Dusty goes to Dottie, who discovers that his gearbox was damaged from pushing it too far. This model of gearbox had been out of production for years and was too complex for Dottie to build, which threatened his racing career.
Skipper later took Dusty for a drink at Honkers, the local bar, assuring him that Dottie wouldn't have said what she said if she wasn't sure. Then suddenly, Chug and Sparky drove up, announcing that they're contacting parts suppliers to find his replacement gearbox. Unfortunately, Leadbottom included himself in the conversation, saying that he's willing to offer Dusty his old crop duster job. Skipper tried to politely talk Leadbottom down but the biplane didn't listen to him.
Subsequently, Dusty went on a defiant flight to test his limits, only to make a crashed landing at Propwash Junction airport, causing a fire. Mayday attempted to douse the fire, only for his hose to sprout leaks. Left with no alternative, Skipper helped his friends bring down the water tower to smother the fire.
The next day, government inspector Ryker shuts down the airport for inadequate firefighting personnel. This throws the town into a panic, knowing that planes can't have their Corn Festival with the airport shut down. Skipper attempted to calm the crowd before deferring to Dottie, who announced her plan to refurbish Mayday to meet Ryker's regulations, before adding that their only problem left was hiring a second firefighter, which Leadbottom pointed would be difficult as it was fire season.
The next day, Skipper saw Dusty off as he flew to Piston Peak National Park to get certified as a firefighter. As with the Wings Around the Globe rally, Skipper and his friends kept in contact with Dusty via radio. Eventually, they were forced to admit that no supplier has his gearbox.
At the end of the film, Dusty had gotten certified, as well have gotten a brand new, custom gearbox made by Maru. As the film ends, Skipper watches Dusty and his colleagues with Piston Peak Air Attack perform an aerial show for all of Propwash.
"You looking to be number 51?"
"Go home! You're over your head kid!"
"You're going up against the best racers in the world and some of them don't finish."
"You're sloppy on your rolls. Tight on your turns and straight at your straightaways."
"Never mind. You already lost."
"You've earned it."
"Listen get above the storm.
"IT'S TRUE!! It's true. I only flew one mission."
"Negative Jigsaw 2. Our orders are to recon and report."
"Alright. Lets go in for a closer look but keep your distance."
"Get outta there Lucas!"
"After that I just couldn't bear to bring myself to fly again."
Probably best that I don't.
Well, I may be old but at least I'm not afraid of heights.
Don't thank me. I learned a lot from you than you ever learned from me.
Its an honor to be here.
Dusty, ready to do some flying?
Snap into those turns. There you go.
Dusty. You okay?
Propwash tower this is Jolly Wrench 7. We're a flight of two inbound for a precautionary landing.
Dottie is an excellent mechanic.
The Fill n Fly!
And Dusty be careful.
Dusty, I'm sorry. (When the wrong gearbox was delivered)