2020: Stephen Colbert (D) vs. Donald Trump (R)

[President Johnson]

Democrats in 2020 nominate their own outsider with comedian Stephen Colbert. How does he fare against Donald Trump?

[Alben Barkley]

Mr. Stephen Colbert (D-SC)/Sen. Amy Klobuchar (D-MN): 350 EV, 51%

Pres. Donald Trump (R-NY)/VP Mike Pence (R-IN): 188 EV, 46%

Or at least, I’d like to think that’s what the result would be. I think Colbert could run circles around Trump in the wit/charisma/social media department. The debates would be very interesting. I guess it all comes down to whether Democrats and Democratic-leaning independents are as willing to vote for an “outsider” as Republicans were. I do think Jon Stewart would be a slightly better choice if it has to be a TV comedian though.

[Grassroots]

Trump wins by a large margin over the smug wealthy comedian.

[Some of My Best Friends Are Gay]

Trump wins by a large margin over the smug wealthy comedian.

The irony of a Trump supporter calling someone else smug and wealthy as an insult.

[Grassroots]

Trump wins by a large margin over the smug wealthy comedian.

The irony of a Trump supporter calling someone else smug and wealthy as an insult.

Trump is a billionaire, sure, but there's a reason why wealthy people in this country swung massively towards Democrats in 2016 and continue to do so at state level.

[Mr. Smith]

Colbert just doesn't have it anymore, and a lot of what got him up to the top hasn't aged well.

Jon Stewart on the other hand still holds up.

[One Term Floridian]

Colbert would NOT win. He might even do worse than Hillary. Dems clearly want experience and not a has-been comedian who only does Trump jokes nowadays. He used to be so good too..

[bagelman]

Trump wins. Colbert would lead in most polls, and proceed to lose.

[Alben Barkley]

Colbert just doesn't have it anymore, and a lot of what got him up to the top hasn't aged well.

Jon Stewart on the other hand still holds up.

Yes, this is why I said Stewart would be better. Unfortunately he removed himself from the political arena at the exact time he was most needed.

[Alben Barkley]

Trump wins by a large margin over the smug wealthy comedian.

The irony of a Trump supporter calling someone else smug and wealthy as an insult.

Trump is a billionaire, sure, but there's a reason why wealthy people in this country swung massively towards Democrats in 2016 and continue to do so at state level.

That is because wealthy people are generally better-educated and accordingly saw that Trump would be such an embarrassing disaster for the nation that they would rather forego their tax cuts than vote for him.

Doesn’t change the fact that Trump is the epitome of “smug” and “wealthy,” so the irony remains.

[Alben Barkley]

Colbert would NOT win. He might even do worse than Hillary. Dems clearly want experience and not a has-been comedian who only does Trump jokes nowadays. He used to be so good too..

How could he do worse than Hillary? I think he could play up his Southern ties to at least swing GA/NC toward him if not win them outright, and if he did choose a Midwestern VP like Klobuchar I think he’d have more appeal there than Hillary did. I don’t think some people have fully grasped yet that Hillary’s 2016 performance was pretty much the absolute floor for a Democrat in this day and age. It will be extremely hard for anyone to underperform her.

[One Term Floridian]

Colbert would NOT win. He might even do worse than Hillary. Dems clearly want experience and not a has-been comedian who only does Trump jokes nowadays. He used to be so good too..

How could he do worse than Hillary? I think he could play up his Southern ties to at least swing GA/NC toward him if not win them outright, and if he did choose a Midwestern VP like Klobuchar I think he’d have more appeal there than Hillary did. I don’t think some people have fully grasped yet that Hillary’s 2016 performance was pretty much the absolute floor for a Democrat in this day and age. It will be extremely hard for anyone to underperform her.

Just like how Hillary's southern ties helped her a bunch in Arkansas. Just like Hillary, Colbert would be perceived as a New Yorker by much of the South because of his full-time gig of hosting the Late Show in NYC.