Henry & Me
Jack (Austin Williams) is an eleven-going-on-twelve year old boy living a privileged life in upstate New York. He and his parents (Joseph Gian and Lucie Arnaz) are major fans of the New York Yankees and have attended many of their games. As he and his father are called to dinner, Jack goes through a temporary state of anemia and drops the ball. His parents are convinced that something is terribly wrong with their son.
The scene switches to Jack in the hospital, where he has contracted cancer to the point where he is completely bald. As he is carted away for an operation, his parents stay behind, and his chaperone Nurse Cyndi (Cyndi Lauper) sings a jaunty tune of "Take Me Out to The Ball Game" to no avail of lifting the boy's spirits. She leaves Jack outside the room, but not before she treats Jack with a sedative to give him "sweet dreams". Unhappy with the hardships brought upon by his newly contracted illness, Jack contemplates the (seemingly) final moments of his life until he is greeted by a guardian angel taking the form of a Yankees executive named Henry. At first, Jack is hesitant to watch the game while he waits, but unwittingly accepts Henry's offer and the man takes him into a imaginary plane of existence where the 20th century is timeless, illness has no existence, the Yankee players of the past are alive and well and most of all, his hair is back.
Henry and Jack's first stop is early 1930, where they meet Babe Ruth (Chazz Palminteri) in a small field surrounded by corn. He convinces Jack to take the bat, and after a nervous fib about a peanut allergy, strikes out three times. Babe convinces him to try again, yet this time, his fellow teammates laugh Jack off for his age. After successfully stealing home run, Jack bids goodbye and rides off in Henry's 1935 Cord 810 convertible for a fun-filled drive into the skies.
Jack and Henry's next stop is mid-1960, where, to Jack's surprise, the original Yankee Stadium is still standing next to the new one. Then in the Yankees' locker room, he meets Lefty Gomez (Luis Guzman), Mickey Mantle, Bobby Murcer and Thurman Munson. Again, Jack is forced into a position on the team, this time to throw the ball from the pitcher's mound. When an actual game ensues, Munson encourages Jack to pitch the ball to Mantle, but he refuses (by saying that he is not a real pitcher). Despite Jack's inexperience, Munson and Jack continue with an upbeat exchange of words until Jack's blood pressure starts to drop, realizing that the game he is fighting for is his life in the physical world. A short montage set to a ballad version of "Time After Time" shows Jack in what appears to be Heaven, watching several moments of his life up to the hospital with other kids, and making him concerned for his parents. When he asks Cissy, a girl he met on Henry's subway train, if she misses her mother and father, she replies "every day", implying that she too is dead and is living in the imaginary world as a spirit. Cissy and some other baseball kids bid Jack goodbye, but not before she shouts back "We're all rooting for you!" With that, Jack wins the battle, and the game.
Automatically transported to the present, Jack meets the elderly George Steinbrenner, who offers him a place on the team. With the permission of the other team members, among them Yogi Berra, Reggie Jackson and "Goose" Gossage, encourage him to be a winner. Magically outfitted with a real Yankee uniform fit for his size, Jack soon finds himself playing alongside Curtis Granderson and Hideki Matsui in a large scale game against the nondescript Boston Red Sox. After the Sox pitcher tips the pitch, causing Matsui to hit the ball into the team bench, Jack quickly whispers Babe Ruth's words into Matsui and later on, he bats the ball so hard it goes straight into the hall of fame.
Nighttime falls and Jack asks Henry if he can meet Joe DiMaggio, Roger Maris and Billy Martin, but Henry suggests saving it for another time and decides to have Jack return home. With an impending rainstorm reflecting the borderline of his decision, Jack is unwilling to return to his unhealthy life and considers staying where he can give his body all the health and exorcise he deserves. After running off, leaving his cap behind, Jack is found by Henry in his chair and reveals that he is Lou Gehrig, another player stricken by disease. Taking his advice that he should keep playing for his life, Jack finally gives in and waves goodbye to Henry, Lefty and Babe Ruth, who arrive just in time to see the boy leave into the real world.
Now back in the hospital, Jack wakes up to the joy of his parents and to his surprise is visited by the team. Although Jack is confident that his hair will grow back, Mr. Steinbrenner gives him the right of being called a New York Yankee with a pin, the same kind worn by Henry.
In a post-credits scene, Henry and Ruth pick up Mr. Steinbrenner in his Cord.
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