Exclusive Excerpt from Supernatural: The Official Companion Season 5

“‘Two Minutes to Midnight’ was a lot of fun to work on,” says executive producer Sera Gamble. “It was like two episodes in one because we had to handle two Horsemen in the same episode. We had a lot of stuff to cover. When we realized that we were going to have Crowley make a deal with Bobby in that episode too, which I believe was a pitch that came from Ben Edlund, that became my favorite thing in the episode.”

Of course, crossroads deals have to be sealed with a kiss. “Mark Sheppard was game for it,” says executive producer Phil Sgriccia. “We had a good time with him. I shot it on an iPhone just off to the side, as if Crowley was holding his hand away from them when they kiss. I did multiple takes just to make sure that there was an ick factor for Jim and Mark while we were doing it! We had to put them through a little bit of hell. It was quite funny, and the crew was giggling the whole time.”

Kissing Sheppard was “stubbly, and he was the one who used tongue,” Jim Beaver deadpans. “No, seriously, it was a bit uncomfortable, mainly because we had to hold the pose for quite a while to get a good photo, and that kind of thing is awkward even if you’re kissing a girl.”

At one point during the shooting of this episode, Beaver probably wanted to slap two guys — specifically Jensen Ackles and Jared Padalecki. “If we get an opportunity to make things difficult for Jim, we definitely take advantage of that,” says Ackles. “On his coverage, we totally changed all the dialogue, so he had to try to remember his lines without having any of the cue lines. When the cameras are off us, all bets are off, especially with guys that we know can take it. So a lot of times it’s, ‘Let’s see how long they can last without laughing in a serious scene.’ We’ll change the words up or we’ll start saying their next line before they say it, which really just throws people off. We like messing with people — we don’t like them to be too serious.”

Even Death doesn’t take things too seriously on the show, chatting about the Devil over pizza. “They were pretty good-tasting pizzas,” Sgriccia says. “Jensen wanted to take one home with him at the end of the day.” Sgriccia knows good Chicago-style pizza too, since he used to live in Chicago. “When I lived there, I had my favorites,” he says. For the episode, “We found a place in Vancouver that called themselves Chicago’s Deep Dish Pizza, and their pizza was as close as we could get, but we wanted them to make it an inch thicker than they normally made it, so they did it for us special.”