While the ESPYs celebrate the best in sports each year, they also serve up some incredible celebrity moments. In honor of the 27th Annual ESPY Awards on July 10, 2019, Wonderwall.com is taking a look back at some of the most talked-about celebrity moments, from those that made us laugh to those that pulled at our heartstrings, starting with one of the most watched ESPYs speeches ever: Caitlyn Jenner's acceptance of the Arthur Ashe Courage Award in 2015. Though the former athlete was once best known for winning a gold medal in the decathlon at the 1976 Olympics, she became more famous in recent years for her role as the patriarch on the E! reality TV show "Keeping Up with the Kardashians" and her subsequent gender transition. At the ESPYs — her first public appearance since announcing her transition — Caitlyn received a standing ovation during her 10-minute speech. "Trans people deserve something vital; they deserve your respect," the then-65-year-old said as nearly all 10 of her kids and stepkids watched from the audience. "From that respect comes a more compassionate community." She offered herself up for ridicule. "If you want to call me names, make jokes and doubt my intentions, go ahead, because the reality is I can take it," she continued. "But for thousands of kids out there coming to terms with the reality of who they are, they shouldn't have to take it." Keep reading for more…
Jamie Foxx serenades Serena Williams
In 2003 and 2004, Jamie Foxx hosted the ESPYs — and he was perfect for the job. In 2003, he started the tradition of roasting athletes, which has continued up until today. He acted as "Coach Do Dirty" both years, jabbing athletes much to the delight of the audience, who roared with laughter. He also performed "Can I Be Your Tennis Ball" both years, a love song he sang to tennis star Serena Williams. The 2004 performance ended with Serena joining Jamie on stage to slap his behind with a heart-shaped tennis racket and get a lap dance from the actor.
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Destiny's Child invites Allyson Felix and Serena Williams on stage
The 2005 ESPYs ended with a show-stopping performance by Destiny's Child. They were singing "Lose My Breath" when tennis great Serena Williams and Olympic track star Allyson Felix joined them, matching them in black looks and heels. "[Serena and I] were asked to do this little walk-out thing with Destiny's Child," Allyson recalled in 2016. "We were both totally out of our element, like, what are we supposed to do exactly? … It's like, what am I doing up here?" Regardless, she and Serena strutted and posed with the singers like total naturals, blowing everyone away with the perfect marriage of music and athleticism to close the show out.
Ben Affleck wears his wedding ring after announcing divorce
Ben Affleck made headlines when he wore his wedding ring to the ESPY Awards in 2015 despite having just announced plans to divorce Jennifer Garner days earlier. Ben presented retired baseball player Derek Jeter with the Icon Award and referenced his broken heart — but not because of his failed marriage. "Boston fans can be many things," Ben said, referring to himself, "but we know baseball and we respect those that play the game the way it was meant to be played. He broke my heart 100 times, if not more. And he broke it again when he retired, because he was absolutely one of the very best ever to play the game of baseball."
Drake does a kiss cam
Host Drake opened up the 2014 ESPYs with a monologue that had one particularly memorable moment. Drake poked fun at Lance Stephenson blowing in the face of LeBron James during the 2014 NBA playoffs by appearing on the "Lance Cam" (his version of a kiss cam) and blowing in his face as a supposed sign of respect. Lance wasn't the only audience member who got in on the "Lance Cam" action — Drake also did a "Double Lance Cam" with NBA star Paul George as the recipient.
Will Ferrell accepts award as Tiger Woods
In 2008, Tiger Woods took home the best male athlete award for the fourth time, but it was not the golfer who accepted the trophy — it was funnyman Will Ferrell. "People are always asking me, 'Tiger, how do you do it?' And my answer is, 'Shut up.' I ask the questions around here. I'm Tiger Woods," Will joked as he accepted the award. "All I did was purposely sever my ACL and broke a bone in my leg, and you know what? I still won the U.S. Open. And that's when even I started to believe it's undeniable, I am the greatest." He closed out his hilarious speech with, "What can I say? I'm the best. In your face. Goodnight everybody."
Justin Timberlake sings his way through the opening
Another major highlight of the 2008 ESPY Awards was host Justin Timberlake's opening monologue, which was fittingly done in song. The pop star sang and danced to a mix of jazz, hip hop, gospel and reggae, all the while proclaiming how much he loves sports.
Stevie Wonder presents the best team prize
Stevie Wonder made jokes about switching from music to sports when he appeared at the 2009 ESPYs. There to present the best team trophy, he began with his "last" musical performance. "Let me see if I can read this," the blind music legend quipped as he opened the envelope, earning himself laughs. He then read the winner, in Braille, and presented the award to the Los Angeles Lakers.
Jay Leno gets emotional during award presentation
Comedian and late night host Jay Leno's emotional presentation of the Jimmy V award for perseverance and best male athlete with a disability was a top moment from the 2011 ESPYs show. It went to Anthony Robles, who was born without a right leg — he won the 2010-2011 NCAA wrestling title with a perfect 36-0 season when he was at Arizona State University. "Every soul who comes to earth with a leg or two at birth must wrestle his opponents knowing it's not what is, it's what can be that measures worth. Make it hard, just make it possible and through pain [I'll] not complain. My spirit is unconquerable, fearless I will face each foe, for I know I am capable. I don't care what's probable, through blood, sweat and tears, I am unstoppable," Anthony said in his acceptance speech. Jay later had the athlete as his guest on "The Tonight Show."
Bill Murray accepts award on behalf of the Chicago Cubs
Bill Murray, a die-hard Cubs fan, was over the moon when his beloved baseball team won the World Series in 2016, ending a 108-year drought. In continuation of his celebration, he ended up accepting their award for best moment during the 2017 ESPYs. "108 years is hardly a moment," Bill deadpanned after accepting the award from Nick Offerman. "This was the culmination of 108 years of momentum… by momentous men." Decked out in Cubs apparel, the comedy star thanked each player by name, after which he chugged a beer with Nick and poured the rest on his head.
Robin Roberts accepts the Arthur Ashe Courage Award
Today, Robin Roberts is known primarily for her achievements in journalism, but before she was an anchor on "Good Morning America," she was a star college athlete-turned-reporter and anchor on ESPN's "Sportscenter." Following her fights against breast cancer and myelodysplastic syndrome, she was honored at the 2013 ESPYs with the Arthur Ashe Courage Award. LeBron James presented the prize to Robin. "Those of us who are fortunate to have overcome some form of illness or adversity are told that we are strong. I didn't find that strength on my own," she said during her acceptance speech. "It was the kind that grew with every kind word of support — every tweet, every email, every phone call. … Through it all, I learned that strength, true strength, isn't when you face down life's challenges on your own, it's when you take them on by accepting the help, faith and love of others and knowing that you are lucky to have those."
Peyton Manning spoofs "The Blind Side"
NFL star Peyton Manning teamed up with movie star Sandra Bullock in 2010 to spoof the film trailer for her award-winning emotional drama "The Blind Side," which was renamed "The Dark Side" — a thriller version. The spoof pegged Sandra as a kidnapper of football players and Peyton, showing off his acting chops, as her latest victim.