The source photograph was taken by Associated Press photographer Stephan Savoia on September 11, 2009, during Jordan's Basketball Hall of Fame induction speech in Springfield, Massachusetts3. Throughout the speech, Jordan cried repeatedly while recounting stories from his career2.

The image sat mostly untouched for a few years. On April 23, 2012, someone submitted an image macro titled "Sad Michael Jordan" to MemeCrunch, featuring the unedited crying photo with the caption "Why / Did I buy the Bobcats?"2. This was the first known meme use, riffing on Jordan's purchase of the then-struggling Charlotte Bobcats franchise.

The photoshopped head-on-body format that defined the meme didn't appear until 2014. According to Wikipedia, posters on the internet message board Boxden.com first started cutting out Jordan's crying face and pasting it onto other people's heads3. On November 7, 2014, The Coli Forums member At30wecashout posted a collection of Crying Jordan examples2.

The meme's biggest mainstream moment came on November 22, 2016, when President Barack Obama awarded Jordan the Presidential Medal of Freedom. Obama introduced Jordan as "the guy from Space Jam" and directly referenced the Crying Jordan meme during the ceremony2. A photograph captured Jordan actually crying during Obama's speech, which triggered a new wave of Crying Jordan photoshops using that very image2.

Athletes embraced the meme too. Draymond Green, Jordan Spieth, and Schoolboy Q have referenced it in interviews3. Players like Stephen Curry, Jon Jones, and Roberto Luongo used the image self-deprecatingly on social media after bad performances3.

The meme inspired physical products. In mid-April 2016, artists Sherman Winfield and Andrew Weiss launched the "Crying Kicks" Tumblr blog, showcasing Air Jordan sneakers with the crying face embroidered on the tongue2.

In March 2018, the meme surged again when Loyola-Chicago lost to Michigan in the Final Four. The team's 98-year-old chaplain, Sister Jean, had become a national sensation for her courtside cheering. After the loss, photoshops placing Jordan's crying face on Sister Jean flooded Twitter, with sportswriter Darren Rovell's version pulling over 4,700 retweets and 11,000 likes2.

After Game 6 of the 2021 NBA Finals, a media producer bought the domain CryingJordan.com and set it to redirect to Chris Paul's profile page on the Phoenix Suns website after his team's loss to the Milwaukee Bucks3.

The meme also lived on in community spaces. Facebook groups like "Crying Jordan Meme Fans" kept the format alive, and the image inspired similar meme faces including "Uncle Denzel," "Uncle Shay," and "Big Ern"3.

What makes Crying Jordan unusual among memes is its five-year incubation period. The source photo existed from 2009, but nobody thought to weaponize it until 2012, and even then the 2012 MemeCrunch post was just using the unmodified image as a reaction2. The creative leap of cutting out Jordan's face and pasting it onto other people didn't happen until forum users on Boxden.com innovated the format in 20143.

The meme's appeal ran deeper than just a funny face. Media critics pointed out that the joke works because it shows "the ultimate alpha in a vulnerable position," and that people "simultaneously mock and celebrate a masculine star who expresses vulnerability"3. Jordan built his entire brand on being an invincible winner. Seeing his sobbing face plastered on a losing team's logo hits different because of that gap between his competitive legend and his emotional breakdown.

The physical world caught up fast. In mid-April 2016, artists Sherman Winfield and Andrew Weiss launched "Crying Kicks," a Tumblr blog showcasing custom Air Jordan sneakers with the Crying Jordan face embroidered on the tongue2. The sneaker culture crossover was a natural fit given Jordan's status in both basketball and fashion.

After Game 6 of the 2021 NBA Finals, when the Milwaukee Bucks defeated the Phoenix Suns, a media producer purchased CryingJordan.com and set it to redirect to Chris Paul's profile on the Suns website3. Someone also built an open-source mobile app called "The Crying Jordan Meme Generator" that let users paste Jordan's face onto any image, and it was downloaded by several thousand people3.

The meme's most emotional moment came on February 24, 2020, when Jordan delivered a eulogy for Kobe Bryant at the Staples Center in Los Angeles. Jordan began crying during his tribute to his close friend, then paused and told the crowd: "Now he's got me. I'll have to look at another crying meme. I told my wife I wasn't going to do this because I didn't want to see that for the next three or four years. That is what Kobe Bryant does to me"3. The crowd laughed through their own tears. It was probably the only time the Crying Jordan meme made people emotional rather than amused.

Professional athletes leaned into the format over the years. Stephen Curry, Jon Jones, and hockey goaltender Roberto Luongo all posted Crying Jordan edits of themselves after bad games or losses3. Draymond Green, Jordan Spieth, and Schoolboy Q referenced the meme in interviews3. The image also spread beyond sports into political commentary, getting applied to Barack Obama and Marco Rubio among others3.