So I’m writing this from my current ‘office’: a guesthouse, although not the guesthouse I originally started out in, which didn’t work out for reasons I won’t bore you with here.
This place is lovely: kind of old Bel Air rustic, tucked across a little stone courtyard from the main house, sunlight filtering through various tangles of green, two young bulldogs snuffling around the faded red brick. It belongs to this dude, who was telling me about his upcoming trip to Sundance to screen the movie in which he plays himself. “I literally play myself,” he informed me over omelettes at an outdoor Brentwood cafe, the server bringing out three eggs to give to the bulldogs, while I struggled to collect my aching self in the wake of a brutal bootcamp-style exercise class held at a nearby studio. He told me how these guys gave him a script to read and he assumed, as any intelligent person would, that they were angling for money to fund it. No, they told him, they just want him to be in it, and sure enough, as he flipped through the screenplay while pacing on the treadmill, he came to himself on page 30: …a spry Jason Calacanis leaps onto the stage… The movie takes place in the dot.com world of 2002, in which Jason first made his mark (albeit not his wealth) through a Silicon Alley publication….Or, as Jason so modestly put it the first time I met him, “as a kingmaker.”
Don’t know what the film is called (Jason, when you read this, feel free to comment on the title…) but it stars Josh Hartnett as the aspiring dot.com mogul. “He’s very nice,” Jason’s cherished wife, Jade, told me. Jade had visited the set. The fact that Hartnett was apparently shirtless while chatting to Jade would not escape Jason’s attention, nor his later narrative about the experience.
“But it turns out I play myself very well,” he told me.
And of that I have no doubt.