At first I thought this was an obvious question, but then watching Roger dance last night I for a moment thought maybe he really is happy?

I took that gesture as a big FU to everyone based on Don's earlier comment about what everyone really thought.

I think Roger wants to believe he's happy. After all, he's rich and sporting a young trophy wife. What more could an old lothario want?
But we saw last night that underneath he's still insecure and jealous. It lit up when he saw Don (a young lothario) with his trophy, and couldn't let it go.
Second, he has to endure the enmity of his other family towards himself and Jean, even as he foots the bill for his daughters wedding.
And third, his position at SC seems to be becoming superfluous at best, and perhaps he's afraid of being pushed out. As Don asked, "What have you done today? What have you had to do all week?"

On another note, blackface? Really? Even in 1963, that had to be in extremely poor taste. I think the point of it was to reinforce Roger's decision making ability is becoming in doubt.

Re: blackface - I'm not so sure that it might not have been socially acceptable.  Most everyone seemed to be genuinely enjoying Roger's performance.  I can remember an episode of "All in the Family" (showing my age - must have been in the mid 70's) that commented on this practice in its own inimitable way.

jkerouac59
While I watched that scene with Roger dancing the night away
I think you're right I think it was a big FU to everyone
At first I thought it shows how much they love each other but I don't think they do
I was really shocked with the blackface thing
even for the 60 that was in bad taste wasn't it?


NG

I don't think the early 60's were enlightened AT ALL - this was probably considered the height of high humor.....Poor Roger - he had two women - Mona and Joan - and now he has a volatile child in Jane.  He'll put on a good show just to try and prove to everyone that what he's done is smart.

Don't comment often, but the black face was in poor taste in the early '60's. Even in far off southern Oregon (where I was a wee nipper at the time), it would have been considered bad form. I think in cosmopolitan NY around sophisticated, educated people, it would have been appalling.

Roger has changed his life into what he thought would make him happy.  He has now been told his exterior does not show happiness...at least to one person (Don).  His dance alone with Jane at the end of the episode shows his willingness to appear foolish to the world and serve as the protector of a child-like individual who needs to be held...and laughs at his stupid jokes and silly faces.  Not such a bad situation for an old guy with a bank account full of money.
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Hmm yeah I don't think he's truly happy, that's why he (and everyone else) keep grasping at straws... I agree it was a big FU.

I would imagine that blackface must have been unacceptable in normal circles in the 60's (especially New York) since we just saw Kinsey go down to Alabama for some civil rights protests... on the other hand, we do know that Roger's wedding was a party of "republicans" as the man at the bar said... so we know most of the men were at least fairly conservative (as in not liberal and called everyone not like them communists) and if the average age was around Roger's (50's?) then possibly they grew up on blackface in the 20's-30's and that's why they "appreciated" his "humor".  That was a shocking image though...

I have a feeling that Jane is only 'wife #2'. 
It will not last very long,
and Roger will have more unhappy relationships. 

And, I don't see Joan's wedding ever happening.

madmaam: I too feel that Roger will dump Jane quicker than one can say her name and soon he will be working on wife number three.

That would mean that Roger would have to give up half of his half from the first marriage. I'm not sure he's willing to do that; or admit a mistake.