Explain this Black Jeopardy joke

Link: Black Jeopardy with Tom Hanks - SNL - YouTube

At about the 2:45 mark, the answer is “Caitlyn Jenner says she wants to be on the cover of Essence magazine”.

Keeley (correctly) answers “What is mmm, I don’t know… you can’t do everything!”

So far so good, I get it. Jenner has been a man and a woman but so far as I know not black.

But then Darnell says, “That’s right, but there was a time though.” Keeley agrees. And then Doug says, “Oh yeah, I remember”.

What “time” are they referring to?

The era when blackface was considered acceptable/funny?

My vote is: "But when he was a Gold Medal athlete doing all 10 Decathlon events, and a fine piece of Man on a Wheaties Box, I thought he could do everything. "

???

I think he’s referring to the Obama presidency.

Thanks for the answers so far but I don’t see how blackface or Obama could put Jenner on the cover of Essence.

[sup](Unless Jenner performed in blackface and I don’t know about it.)[/sup]

I don’t see what Jenner actually having performed in blackface has to do with it. The joke is about Jenner being all over the press, seeming like she can do everything. But the one thing she can’t do is turn black. Then, on reflection, they realize there was a time… and they turn to the oldest guy in the room for confirmation, a guy who might be old enough to remember blackface.

I see the point.

The episode aired right before the election (which made the Tom Hanks character so funny and almost palatable), when everyone thought Hillary was going to win, so that’s not it. I vote for “decathlon” winner.

The “decathlon” thing doesn’t make any sense. The gag is based on Jenner seeming to be unstoppable now, reinventing herself and all over the press now. Not that her abilities are diminished now that she has retired from athletics - quite the reverse.

Except that she can’t turn black, a requirement for getting on the cover of Essence. (Which is hardly something being a white male decathlete would help you with, anyway.)

I don’t think it’s a good joke, but I have no doubt that it’s about blackface.

My 2¢: Blackface. “He/she could have been black at one time.” Redneck replies “Oh, yeah. . . I remember the good ole days.”

I thought that was the joke: that, after pretty much dismissing the idea out of hand, he grants that there was a time – back in '76 – when Jenner was so amazingly cool that the owner of Essence Magazine maybe would’ve said, “The cover? Could be.”

“After this we’ll play the national anthem and see what the hell happens”

So prescient that this joke still works today. Also, what a great sketch…Black Jeopardy’s best by far

Yep, this one has been the best so far; the one w/ Louis CK is good too.

Given the two competing theories I’ve come to believe it’s this one. Doug is not old enough to remember blackface.

Yeah, I don’t even know.

I just watched the clip. Darnell just says “I mean, there was a time”. That’s a bit vaguer than the quote in the OP.

I’m going to break from the crowd and posit that “there was a time” is an expression of longing for the good ole days. As in, “There was a time when Essence was a magazine for and about black people, but now we have white folks thinking they get to be on the cover.” Or “There was a time when we used to tell attention whoring weirdos to sit down somewhere and STFU, but now we have to pretend they are normal.”

These are not politically correct expressions. It wouldn’t be funny if Darnell said these things. But “There was a time” allows you to insert whatever you want and then laugh as Doug cosigns it.

I’m with monstro. I took it as a more conservative take on the matter: back in the day a man was a man, a smoke was a smoke, a phone call cost a dime, etc., but now it’s all gone mad.

She could always identify as black. I mean, it worked for Rachel Dolezal.

For certain values of “worked”

First, I respect monstro’s perspective.
Second, I did not purposely misrepresent Darnell’s words. I just quoted it as best as I remembered it.

But to monstro’s point, I’m not getting it. Keeley says ‘you can’t do everything’. Darnell says ‘there was a time’. To me that means there was a time she could have made the cover. Opposite of what monstro is positing