September 14, Bryson Gray tweeted a video of him rapping about supporting Trump, along with “#MAGAChallenge” encouraging his followers to make their own raps about Trump. In an interview with The Daily Dot, Gray stated, “I think the MAGA challenge is doing what everybody expected Kanye West to do for the [Trump] campaign.” West has not responded to this comment, however he is one of the few famous rappers who has recorded a song in support of Trump, “Ye vs. The People.”
Trump has a long history of being used in rap music. The Washington Post cited that Trump's name can be found in rap songs all the way back in 1989, with songs “Lie-Z” by Fat Boys and “My Word is Bond” by Ice-T both mentioning Trump. Trump has been name-dropped in many rap songs since then. A majority of these songs using Trump's name show him negatively, most notably would be the 2016 song “FDT” by YG and Nipsey Hussle.
One of the most famous participants in the #MAGAChallenge is Isaiah Washington. Washington is best known for his role as Dr. Preston Burke on Grey’s Anatomy. ABC chose not to renew his contract for the show in 2007, due to his use of a homophobic slur in an argument with his co-star, T.R. Knight.
Trump finally reacted to the #MAGAChallenge on November 8th in a tweet inviting the winner of the challenge to perform at the White House. There has been no indication on when these winners will be announced or when they will be performing at the White House.
This isn’t the first time Trump has offered meeting him as a prize to winning a contest. According to Popular Informer, Trump’s campaign has held 15 contests to win a free meal and to meet the President. In the article by Popular Informer, claims that there is no evidence that anyone has won these contests. Trump campaign Communications Director Tim Murtaugh responded to this saying “people win the contests each time,” but not providing any evidence. The Daily Caller did post an article in which two contests winners, Joanna Kamis and Chris Chavez, discuss what winning the contests was like. The Daily Caller article was posted on November 6th, and as of November 15th, these are the only two contest winners that have come forward.