WI: By 2016 Jon Stewart is President of the US and David Mitchell is Prime Minister of the UK

With a PoD during or after 2006, please figure out a logical series of events that would lead The Daily Show's Jon Stewart and 10pm Live's David Mitchell to jump from being satirical comedians to active politicians and, within a decade, reaching the highest office in the land for their respective countries. I'm assuming that a very big and dramatic event would have to persuade them to make the leap into politics.

Bonus points for detail.
 
Don't know about Mitchell, but I can think of a path for Stewart. First off, a Republican wins the 2006 New York gubernatorial election. IOTL, Elliot Spitzer won against John Faso by 40-point margin, so a few factors will need to change (say, the Republicans nominate Bill Weld instead of Faso and/or Spitzer's prostitution scandal comes out earlier). Assuming Hillary Clinton still becomes Secretary of State in 2009 or she becomes president, a replacement for her in the senate will be appointed by the Republican governor, and that replacement will face reelection in 2010. I can't really think of what could motivate him to do it, but Stewart could run for the seat as a Democrat and win, then run for president in 2016.
 
I could imagine Jon Stewart running on a 'Groucho Marx' style campaign of 'Don't vote for me - I don't want to live in a country with me as the President and neither do you'

Needless to say - landslide victory with over 60% of the popular vote

Several Fox News pundits are hospitalised when the results come in

David Mitchell....this one is more difficult....becomes a junior minister after standing in a local by election....and is then thrust into the PMs spot following the tragic deaths of a number (quite a large number in fact) of other cabinet ministers

"Sir most of the Cabinet is dead - that makes you Prime Minister - the Queen would like to see you in 30 min.."

"Hmm What...no no no" laughs "I'm David Mitchell - you've mistaken me for someone else"

"yes um well...the car is ready sir and the queen really does not like to be kept waiting"

Then you get this at Prime Minister's Question time
 

shiftygiant

Gone Fishin'
On Mitchell, he wanted to be Prime Minister or Comedian, only settling on the latter once he went to Cambridge and met people who wanted to be comedians. He was rejected by Merton College in '93, and instead decided to go to Peterhouse. Obvious PoD is for Mitchell to be accepted into Merton and reads history there, and involves himself in Oxford University politics instead of theatre. He'd probably end up in Labour, maybe get selected for a seat in 2001 or 2005 if he's lucky, and if he's luckier he might win and hold it in the following General Elections.

I'm not sure, however, how he becomes Prime Minister. He's unlikely to be the Prime Minister in or before 2017, being only 42- he might have a chance if he's made a junior minister in the later stages of the New Labour Government, gaining Shadow Portfolio in opposition, but a path to Leadership is a bit difficult to chart.
 
OTL's Mitchell is a Lib Dem, or at least leans that way, which doesn't bode well for PM ambitions, so he'd either need to have different politics or try and fit into the broad church of one of the other two parties. I get the sense he is socially liberal and environmentalist (simply from a realist perspective) but also believes in a degree of fiscal restraint, so I in a sense I could see him fitting in on the left of the Tories as on the right of Labour.
 
Jon Stewart was roommates with Anthony Weiner, perhaps he convinces him to enter politics.
 
Honestly, Trump's win IOTL kind of ruined any requisite for holding office before that. I was thinking this...

Jon Stewart at the time of his retirement was already popular. Perhaps realizing that Donald Trump is becoming front-runner, Stewart decides to use his fame for good and launches on his finale a campaign for the Democratic nomination for President of the United States. At first (Like Trump's) his campaign is treated as a joke by the media, but unlike Bernie Sanders has a really good following among young people, and is more relatable compared to the other two major candidates, as he has school-aged children. Although he is outspoken, his views are less radical than Sanders' and he lacks the scandals that Clinton has. The primaries are a tough battle, but after a few debate performances he surpasses O'Malley and Sanders and goes head-to-head with Clinton. Going all the way to California, he ekes out a victory against her, winning the nomination.

Selecting Amy Klobuchar as his running mate, Stewart goes up against Trump. The comedian against the reality star, and Stewart with his sharp tongue and humor manages to win over the American people. Showcased are his charitable acts and general goodness, and without Trump surrogates being able to pull the "But Hillary Clinton..." style attacks on him, he manages to perform well. He ekes out a bare victory over Trump in November, winning Florida, Michigan, Wisconsin, and Pennsylvania.
 
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