- A reclusive old Navy Corsair, Skipper was an ace flier and top instructor of the esteemed Jolly Wrenches squadron until a combat mission in which he was the only survivor of his squadron left him grounded for life. These days, Skipper keeps to himself, but his quiet existence is turned upside down when an ambitious and persistent Dusty solicits Skipper's aerial expertise—and gets a few life lessons in the process. But Skipper—who's never really come to terms with his past—finds that he has a few things to learn, too, and while coaching Dusty to fly faster and smarter, the teacher becomes the student.
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.
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.
When Dusty takes on his old sprayer for an air show advertising Propwash's signature fertilizer, Vitaminamulch, Skipper compliments him for his good flying. Suddenly, Chug rolls up in an eccentric fanboy getup, which Skipper points out that everybody can see him. However, Dusty and Chug were more excited by their upcoming special guests, Air Devil Jones and Vandemonium, who were going to do a loop landing onto a moving van, which Skipper derided as crazy. However, Leadbottom and Sparky sadly announce that Air Devil Jones and Vandemonium were held up in Flagstaff. Soon Leadbottom gets the idea to pass off Dusty and Chug as Air Devil Jones and Vandemonium, albeit poorly.
- Skipper's make (F4U Corsair) and Skull and Crossed Wrenches insignia on his engine cowling are clearly based upon the World War II US Navy Figher Squadron VF-17 ("The Jolly Rogers"). Skipper even has "VF-17" stenciled on his rear fuselage. In the photo, you can compare Skipper with "Big Hog", the Corsair flown by Cdr Tom Blackburn, CO of VF-17.
- In the Japanese trailer of Planes, Skipper was voiced by Takaya Hashi (土師孝也), but Tarō Ishida (石田太郎), the Japanese actor of Skipper, passed away from a heart attack on September 21, 2013, while Japan was producing Planes in Japanese.
- Skipper is somewhat similar to Doc Hudson from the Cars franchise. They are both elderly vehicles who mentor the protagonist (Doc to McQueen and Skipper to Dusty) in preparation for big races and also reveal a tragic past to them (Doc revealing to McQueen that he was a former racecar who crashed and put out of season, Skipper revealed to Dusty that he only flew on one mission in which he got shot down).