Caitlyn Jenner's ESPY Awards history: 'It's all about entertainment'

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Caitlyn Jenner ESPYs Rewind: All the Times Caitlyn Hit the ESPYs

Wednesday night's ESPY Awards will mark Caitlyn Jenner's public debut, but it's far from the first time that the former Olympian has attended the sports awards show.

"You have to give a performance when you go out on the athletic field and you have to give a performance when you go out in front of that camera," Jenner said at her first ESPYs in 2002, when she walked the red carpet with then-wife Kris as her date. "It's all about entertainment, it's about the show."

WATCH: Caitlyn Jenner's Arthur Ashe Courage Award Stirs Up Controversy

Jenner is not expected to walk the red carpet this year before receiving the Arthur Ashe Courage Award, all part of controlling her heavily-guarded public image. But she's no stranger to scrutiny.

"You're going to be scrutinized, the media's tough," Jenner told ET at the awards show in 2008. "They're going to write either positive or very negative. In the middle, who cares? So you just have to be very careful with yourself and what you do."

See Caitlyn out and about:

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Caitlyn Jenner's ESPY Awards history: 'It's all about entertainment'
BEVERLY HILLS, CA - FEBRUARY 28: TV personality Caitlyn Jenner arrives at the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at Wallis Annenberg Center for the Performing Arts on February 28, 2016 in Beverly Hills, California. (Photo by John Shearer/Getty Images)
BEVERLY HILLS, CA - FEBRUARY 14: Chris Rock, A. J. Calloway and Caitlyn Jenner attend the 2016 Pre-GRAMMY Gala and Salute to Industry Icons honoring Irving Azoff at The Beverly Hilton Hotel on February 14, 2016 in Beverly Hills, California. (Photo by Kevin Mazur/WireImage)
NEW YORK, NY - FEBRUARY 10: Caitlyn Jenner is seen on February 10, 2016 in New York City. (Photo by Ignat/Bauer-Griffin/GC Images)
NEW YORK, NY - FEBRUARY 09: Caitlyn Jenner is seen on the streets of Manhattan on February 9, 2016 in New York City. (Photo by Michael Stewart/GC Images)
RANCHO PALOS VERDES, CA - FEBRUARY 02: Executive Producer Caitlyn Jenner speaks at the AOL 2016 MAKERS conference at Terranea Resort on February 2, 2016 in Rancho Palos Verdes, California. (Photo by Alberto E. Rodriguez/Getty Images)
PASADENA, CA - JANUARY 14: Tv personality Candis Cayne (L) and executive producer/tv personality Caitlyn Jenner speak onstage during the 'I Am Cait' panel discussion at the NBCUniversal portion of the 2016 Winter TCA Tour at Langham Hotel on January 14, 2016 in Pasadena, California. (Photo by Frederick M. Brown/Getty Images)
LOS ANGELES, CA - JANUARY 04: Caitlyn Jenner Hosts Special Screening Of 'Tangerine' at Landmark Nuart Theatre on January 4, 2016 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
Caitlyn Jenner speaks to the Chicago House luncheon at the Hilton Chicago on Thursday, Nov. 12, 2015. (Nancy Stone/Chicago Tribune/TNS via Getty Images)
NEW YORK, NY - NOVEMBER 09: Olympic gold medalist Caitlyn Jenner attends Glamour's 25th Anniversary Women Of The Year Awards at Carnegie Hall on November 9, 2015 in New York City. (Photo by Taylor Hill/Getty Images)
NEW YORK - NOVEMBER 08: Caitlyn Jenner seen at the Soho House for dinner on November 08, 2015 in New York, New York. (Photo by Josiah Kamau/BuzzFoto via Getty Images)
NEW YORK, NY - NOVEMBER 08: Caitlyn Jenner seen leaving 'Therese Raquin' on Broadway in Midtown on November 8, 2015 in New York City. (Photo by Robert Kamau/GC Images)
LOS ANGELES, CA - OCTOBER 27: Caitlyn Jenner attends Logo TV's 'Beautiful As I Want To Be' web series launch party at The Standard Hotel on October 27, 2015 in Los Angeles, California. (Photo by Tibrina Hobson/Getty Images)
LOS ANGELES, CA - OCTOBER 27: (L-R) Chandi Moore, Candis Cayne, Caitlyn Jenner and Geena Rocero attend Logo TV's 'Beautiful As I Want To Be' Web Series Launch Party at The Standard Hotel on October 27, 2015 in Los Angeles, California. (Photo by Gabriel Olsen/FilmMagic)
LOS ANGELES, CA - OCTOBER 27: Caitlyn Jenner attends Logo TV's 'Beautiful As I Want To Be' Web Series Launch Party at The Standard Hotel on October 27, 2015 in Los Angeles, California. (Photo by Gabriel Olsen/FilmMagic)
LOS ANGELES, CA - OCTOBER 03: TV personality and activist Caitlyn Jenner speaks onstage during the Point Foundation's Annual Voices On Point Gala at the Hyatt Regency Century Plaza on October 3, 2015 in Los Angeles, California. (Photo by Jason Kempin/Getty Images for The Point Foundation)
PACIFIC PALISADES, CA - SEPTEMBER 12: Caitlyn Jenner attends the 8th Annual Safety Harbor Kids Polo Classic Fundraiser at Will Rogers State Historic Park on September 12, 2015 in Pacific Palisades, California. (Photo by Michael Bezjian/Getty Images)
LOS ANGELES, CA - SEPTEMBER 03: Caitlyn Jenner is seen on September 03, 2015 in Los Angeles, California. (Photo by gotpap/Bauer-Griffin/GC Images)
LOS ANGELES, CA - JULY 24: (EXCLUSIVE COVERAGE) Caitlyn Jenner attends Culture Club's performance at the Greek Theatre on July 24, 2015 in Los Angeles, California. (Photo by Kevin Winter/Getty Images for Nederlander)
Photo by: Joel Mark/STAR MAX/IPx ©2015 7/16/15 Caitlyn Jenner at The Del Mar Thoroughbred Club. (Del Mar, CA)
LOS ANGELES, CA - JULY 24: Caitlyn Jenner introduces Boy George and Culture Club at The Greek Theatre on July 24, 2015 in Los Angeles, California. (Photo by Tibrina Hobson/WireImage)
Caitlyn Jenner accepts the Arthur Ashe award for courage at the ESPY Awards at the Microsoft Theater on Wednesday, July 15, 2015, in Los Angeles. (Photo by Chris Pizzello/Invision/AP)
NEW YORK, NY - JUNE 29: Caitlyn Jenner is seen in Tribeca on June 29, 2015 in New York City. (Photo by Alo Ceballos/GC Images)
NEW YORK, NY - JUNE 30: Caitlyn Jenner arrives at Patrica Field store in Soho on June 30, 2015 in New York City. (Photo by Raymond Hall/GC Images)
NEW YORK, NY - JUNE 30: Caitlyn Jenner is seen coming out of Patricia Field store in New York City on June 30, 2015 in New York City. (Photo by Raymond Hall/GC Images)
NEW YORK, NY - JUNE 30: Caitlyn Jenner is seen on June 30, 2015 in New York City. (Photo by NCP/Star Max/GC Images)
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"We've been watching Caitlyn since her debut and every interview that she has given has been in a very controlled environment," ET's Liz Applegate weighed in. "She's never agreed to walk the red carpet and that was a very calculated and media-savvy move, because the red carpet is a very brutal place to be. This way she can control what the story is."

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The red carpets were once a family affair for the Olympic gold medalist, who brought a different member of the Kardashian/Jenner clan every year. Back in 2006, her date was the first member of the brood to surpass her in notoriety, stepdaughter Kim Kardashian.

"It's kind of shocking," Jenner said of Kim's new-found fame at the time. "I worked my butt off for years and years and years and you get some recognition and you know, you see these kids today and they're out there. It's a whole different type of generation."

Kim's sister Kourtney Kardashian weighed in on media scrutiny on their family when she was Jenner's date in 2008.

"It's a little frustrating at times when some of the stories aren't always true, but you kind of just have to not take yourself so seriously and just kind of laugh about it," Kourtney told ET.

WATCH: Brody Jenner on Supporting Caitlyn Jenner at ESPYS: I'm There for Her 100%

Scrutiny has continued to follow Jenner in the months since her transition. Critics even claim that giving her the Arthur Ashe Award, making her the third consecutive LGBT recipient, is a ratings ploy by ESPN to cash in on her popularity.

"We've spoken to executive producers, they deny that," Applegate said, adding that Jenner receiving the award is "a really big deal. It sets up the next chapter in her life."

Jenner can always look to her past to help deal with media scrutiny. As attention on her family members grew with the popularity of their reality shows and public personas, she could always be counted on for words of wisdom.

"Don't give 'em any ammunition, that's number one, don't give the media any ammunition because they're going to run with it whether it's true or not," she told ET in 2008. "You just have to be very careful."

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However, it seems Jenner's biggest concern of the night might be what to wear, as she's reportedly tried on 20 dress and skirt combinations for the awards show. No matter what she picks, all eyes will be on her, but Keeping Up With the Kardashians executive producer Ryan Seacrest is sure that she will handle the night with grace.

"There's no way to predict how this is all going to unfold but I think Caitlyn's done an amazing job," Seacrest said.

WATCH: ESPN Producers Explain Decision to Honor Caitlyn Jenner With ESPY Courage Award

ESPYs Producers Explain Why They Chose Caitlyn Jenner for Arthur Ashe Award

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