Several people then play Jenkins, which you probably saw in a much funnier and cuter scene in The Office. I have a feeling Sorkin saw it, anyway. Gary Cooper prefers to play chess during parties. Kendra is kicking his ass. Oh, and then Jim and Will break out their guitars for a jam session... like, the fuck? Am I a freshman in college right now? No. So no lame guitar sing-alongs just because two actors happen to play the guitar. Actually, it's worse than a sing-along because I think they did this song in a studio and now they're lip-synching. Also, they're performing "Sunshine" by Jonathan Edwards, who did this song a whole lot better than those two ever could. (Although maybe I'm wrong about John Gallagher, Jr. My brother saw him perform with a band a few times and said they were pretty good.)
Having wowed the crowd with his awesome guitar skills, Will decides to eat a few pot cookies, as provided by Neal's sort-of-girlfriend, Kaylee. First though, he feels the need to tell the kids that he's only eating marijuana because it's medicinal and he has knee problems due to his amazing pitching prowess when he was in high school. He could throw a "74 mile-per-hour fastball" when he was a junior. Oh really? Because as I recall, Charlie told us that Will graduated college at 19, which means he was, what, 14 when he was a high school junior? "I was an awesome high school athlete," Will summarizes. Ew. He thanks Kaylee for the pot cookie gift -- like, who brings pot cookies to her sort-of-boyfriend's late-middle-aged boss's apartment party as a gift? I hope Kaylee is secretly filming this to give to TMI. But no, she just recommends that Will not eat more than a quarter of a cookie at a time because they're "pretty strong." She gave him like four cookies! Even if he ate one quarter a day, it would take him 16 days to finish them, by which time they would surely be stale. Poor planning. Also, too bad she didn't give Will this advice, like, an hour ago, because he already ate two cookies. Instead of urging him to throw up before he digests way too much pot, Kaylee tells him to "enjoy himself" for the next 12-14 hours. Will's not worried, saying that much like he was a fantastic 13-year-old high school athlete and has an "incredibly high tolerance." Also he just took Vicodin. "Stay away from anything dangerous," Kaylee says. Neal seems to think it's funny that his not-girlfriend just killed his boss.
So Will is a moron, but MacKenzie still manages to be worse because she just got an email from someone named "Mike Tapley" saying "I'm available. Call me," and she assumes he's asking her out when, as we later discover, he's ACN's national security analyst. She complains to Charlie, who ignores her.