The Upside Ending Explained (Spoilers)
While the high of Lily’s continuing presence got Phillip excited in ways he hasn’t been since his wife died, and when Dell got him hookers, she ultimately was a disappointment. I mean, yes, she was beautiful, lovely voice, and was sweet but it was clear she wouldn’t see Phillip as a man. At least not as the kind of man he wanted to be seen. So with the idea of romantic companionship dashed, this sent Phillip into a depression. One which led to him pushing everyone away but, luckily for Dell, this came after Phillip set him up with $50,000, from someone else’s pocket.
With said money, the time Dell spent tinkering with Phillip’s machine, and his knowledge of machinery in the past, he created his own line of electric chairs. A company which we’re left to assume is profitable, and so, when Phillip’s physical therapist asks of Dell to see if he can get Phillip out of his funk, he doesn’t hesitate. The man gave him a second chance, so Dell does the same for him. Leading to Phillip, once more, taking to the air and paragliding with a chair for people with his condition. Maybe not leading to those two becoming friends again but Dell giving Phillip the gift many, even Yvonne, were perhaps too scared to give him – a semblance of his old life back.