She also offered to pay ex-boyfriend 50 Cent’s taxes if he votes for Biden, and said she will sleep with him again too, on the condition that he publicly denounce Donald Trump and vote for former vice president Joe Biden.
(Quick reminder: Vote buying is illegal.)
50 Cent is the stage name of rapper, actor, and businessman Curtis Jackson III.
The back-and-forth played out on Twitter, Instagram, and The Tonight Show, making it a little hard to follow, so we’ve assembled it in an easy-to-read linear chain showing the sequence of events.
On Monday Oct. 19, 50 Cent posted a message telling his 26 million Instagram followers to vote for Trump after he learned that he could potentially face a 62 percent tax rate under Biden’s tax plan. (Instagram later flagged the post with a warning label because it is “Missing Context.”)
On Tuesday Oct. 20, 50 Cent posted a similar message to Twitter, saying that he doesn’t want to be 20 Cent, and that a 62 percent tax rate is a very bad idea.
Handler, 45, replied to his tweet that evening by saying, “You used to be my favorite ex-boyfriend.”
Her reply caught the rapper’s attention. On the morning of Wednesday, Oct. 21 he posted a screenshot of her tweet with the caption: “Oh my God this is effecting my love life now. @chelseahandler I love ya Gator, don’t let Trump and Joe Biden come between us girl.”
(“Gator” is his nickname for Handler. He previously explained to Howard Stern he calls her that because being in bed with her is like wrestling a gator.)
Handler then responded Wednesday afternoon with a quote-tweet by writing: “Hey fucker! I will pay your taxes in exchange for you coming to your senses. Happily! Black lives matter. That’s you, fucker! Remember?”
The offer apparently wasn’t enough to sway the rapper. Two days later, on Friday Oct. 23, Handler took to Twitter to share an article titled “Chelsea Handler Offers to Pay 50 Cent’s Taxes If He Changes Mind on Supporting Trump,” along with the message “This offer stands until Nov. 3rd, Curtis.”
Handler upped the ante during her appearance on the Tonight Show on Friday by implying she would sleep with 50 Cent again if he votes for Biden.
She explained the situation to host Jimmy Fallon by saying that her ex-boyfriend 50 Cent “doesn’t want to pay 62 percent of taxes cause he doesn’t want to go from 50 Cent to 20 Cent.” She then said, “I had to remind him that he was a black person, so he can’t vote for Donald Trump, and that he shouldn’t be influencing an entire swath of people who may listen to him because he’s worried about his own personal pocketbook.”
Handler said that she hadn’t heard back from 50 Cent yet, but she told Fallon that, “I am willing to, you know, seal the deal in more ways than one if he changes his mind and publicly denounces Donald Trump. I might be willing to go for another spin if you know what I’m talking about,” she said while holding her hand up and twirling her finger in a circular spinning motion.
That seems to have caught 50 Cent’s attention. On Saturday, Oct. 24, 50 Cent posted a clip of Handler’s appearance on The Tonight Show that he captioned: “a what, another spin Fu*k Donald Trump, I never liked him.”
A lot of publications are now running with that, trying to portray the story as if 50 Cent retracted his support for the president. But things might not be all that rosy between the former lovers. On Sunday Oct. 25 Handler replied to his tweet by writing: “Honey- does this tweet me[an] we can count on a vote for you for @JoeBiden? I’m happy to discuss this with you privately. My phone number is still the same. Your’s isn’t. I’ve tried calling you.”
Yikes. Her formerly favorite ex-boyfriend changed his phone number and she doesn’t have it.
So to recap: Handler explicitly and repeatedly offered, in writing, to pay 50 Cent’s taxes if he rescinds his apparent endorsement of Trump and votes for Biden. That is most definitely illegal. (It’s also a great deal that he would be foolish to turn down, if it weren’t illegal.)
Handler also offered sex in exchange for voting for Biden, but it’s debatable whether sex with a 45-year-old ex-girlfriend who was once filmed laughing while getting peed on by “American Pie” actor Jason Biggs is a thing of value, so Handler probably isn’t going to be in any legal jeopardy for that offer. (It’s easy to find the uncensored video by googling if you are interested.)
Handler shared the story of getting peed on with Conan O’Brien, saying that, “I thought it was so funny that someone would pee on someone’s face that I was laughing so hard I couldn’t swim away.” She also said, “To me it’s funny that somebody could be that rude to another person, and so that made me really happy.”
Watch the clip to the end to catch Andy Richter’s quick-witted zinger in response to Handler calling him fat.
Handler’s IMDB credits include a sketch comedy show (“The Chelsea Handler Show”) and she also hosted the “Chelsea Lately” talk show. Her new comedy special “Chelsea Handler: Evolution” was released Oct. 22 and is now available for streaming through HBOmax.