Disney's The Kid (2000)

Russ Duritz is a high-powered, successful "image consultant" whose life is suddenly turned upside down when he magically meets Rusty, himself as an 8-year-old child. Rusty is a sweet, but slightly geeky, awkward little kid who painfully reminds Russ of everything he hated about himself when he was a child--a pudgy little crybaby who was the daily victim of the school bullies--an image Russ has worked hard to overcome and consciously forget. Ironically the kid is also unhappy with who his 40-year-old self has turned out to be. He is not at all impressed by his attractive physique, wealth or seemingly important accomplishments. He can't understand the concept of Russ' job as an image consultant, or why he has forgotten about their dreams of becoming a pilot. All he knows is that he grows up to be a 40-year-old loser--an adult without a wife or even a dog!