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Old Lady Jackson 

from Talking As Fast As I Can by Lauren Graham - Old Lady Jackson is when you feel too old and not cool anymore. Say you’re a technophobe and you don’t get technology or you’ve decided going out on a Saturday night isn’t fun anymore. You’ve become a sensible, very mature person. A motherly figure. Someone to blame when you’ve said something out of character and unexpected.
That’s Old Lady Jackson. Old Lady Jackson is coming out. Oh sorry that wasn’t me that was Old Lady Jackson.
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Reverse Michael Jackson 

When you go from being light skinned to dark skinned over time, essentially the reverse of Michael Jackson who went from dark to light skinned.
Guy 1: yo, look at these old pics of Ariana Grande
Guy 2: damn, she really pulled off a reverse Michael Jackson
Reverse Michael Jackson by PythonP February 26, 2021

I'm bad as Michael Jackson. 

A line that Lil Nas X used in his hit song, Holiday.
"Dude you are bad at this."
"Yeah, I guess that means, hee hee I'm bad as Michael Jackson."
I'm bad as Michael Jackson. by IPrpl February 26, 2021

Pulling a Jackson

When you wear pajamas under your pants.
Wearing pajamas under your pants? You're Pulling a Jackson.
Pulling a Jackson by Dose of Dude January 24, 2009

Stone-wall Jackson

When a male is expecting a date to end in sex, and is usually unpleasantly disappointed. Generally the date leaves the male feeling discouraged, and so sad they can't even muster up the enthusiasm to masturbate.
"Damn, I drove 15 miles in a blizzard to get some, and it ended in stone-wall Jackson. I couldn't even muster up the enthusiasm to masturbate!"
"What a bitch."

Make like Janet Jackson and nip out 

To pop out for a brief period of time, like Janet Jackson's nipple at the Superbowl.
I'm just going to make like Janet Jackson and nip out - anyone want anything?

andrew jackson 

The 7th president of the United States. He acted against the ruling of the Supreme Court which recognized the government of the Cherokee Indians and the borders of their homeland. He helped the Georgians to force the Cherokee out of their land, saying such things as, "Let (the Supreme Court) protect them" and "We will light a fire underneath (the Cherokee) so that they will have to move." After being rounded up and placed in concentration camps, many Cherokee starved to death, while others prostetuted themselves for food. Then they began the Trail of Tears or Trail Where They Cried Oklahoma, along which several thousand died. The reason of all this was the anger and selfishness of Georgians who could not accept the fact that the Cherokee had built a government for which the United States government was a model (it had 3 branches of government). Moreover, the Georgians, excited by the Georgia Gold Rush, wanted the gold that was on Cherokee land. It is through his actions that today certain groups of Cherokee Indians now buy back very small portions of the land that is there's, reluctantly using casino money to do so. Thus, Andrew Jackson is another step in the legacy of cruelty, racism, and genocide of American Indians.
Although his actions were horrible, Americans continue to revere Andrew Jackson because he was "a man of his times" and that somehow excuses him.
andrew jackson by John Thiel September 3, 2008