August 2009, in an alternate universe: Ted Kennedy dies; Conan O’Brien has been hosting The Tonight Show for just shy of three months, but it is already clear to NBC executives that, to them, the new guy is just not working out; at the same time, Jay Leno has decided that he doesn’t really want to do The Jay Leno Show at all, so plans for the new show are scrapped, and Leno returns to his old job; Conan O’Brien, more devastated at the news of the death of the great legislator than he is at the loss of his relatively new hosting gig, and casting about for his next career move, makes a brisk, ambitious, and inspired decision: he moves back to his hometown of Brookline, Massachusetts with his family, establishes residency, and announces his campaign for senate, all during the month of September; Coco wins the primary in December handily, and in January 2010, defeats Republican Scott Brown in a landslide.
In this alternate universe that is entirely identical to our universe except for these two wrongs made into one right, the logic of O’Brien succeeding Kennedy is clear to everyone: after the candidacy, victory, and eventual seating of fellow Saturday Night Live veteran Al Franken, the idea of a comedian senator is not just not unusual, but even desirable to Democrats, who find themselves constantly on the verge of tears these days; the commonality between the two men of strong Irish Catholic family backgrounds (Kennedy the youngest of nine children, O’Brien the third of six) is poignant and meaningful for many Massachusetts voters, who take the responsibility of choosing their next senator quite seriously; the Harvard connection means something as well; the state is joyous—ecstatic, even—in welcoming home a local boy made good.
O’Brien brings his entire staff with him to Boston, all of whom transition quite easily, it is reported, from entertainment to politics; the campaign is generally regarded by the public and the media as the funniest in the nation’s history. Scott Brown, on election day in January 2010, is caught on camera chuckling to himself as he leaves the voting booth. He tells reporters that he couldn’t help it—he, like nearly everyone in the state, voted for O’Brien. His opponent’s last campaign speech had been just too hilarious. Coco, the former Cosmo centerfold tells the cameras, deserves to be the next senator from Massachusetts.
Jay Leno, in the meantime, after only a few months of being back as host of The Tonight Show, decides that the franchise itself has been cursed. Its ratings, and viewers, had never quite returned to the levels where they’d once been. The thrill, he realizes, is gone as well; over the summer of 2009, he’d developed a taste for not being on television every night, and for spending more quality time with his vast automobile collection. In January 2010, Leno abruptly quits. (NBC executives, in what is described in a press release as a bold, audacious, and outside-the-box move, hire Mike Huckabee and Sarah Palin away from their jobs at the Fox News Channel as the new Johnny and Ed; the show, and its co-hosts, subsequently wither away into obscurity.) Leno, inspired by O’Brien’s career shift to a life of service, moves back to his hometown of Andover, Massachusetts, bringing with him all of his many cars. Having announced that he, too, is retiring from the entertainment business for good, he begins work as a part-time guidance counselor and shop instructor at Andover High.
(N.B.: Image borrowed from Mike Mitchell.)