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

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)
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)
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)
NEW YORK, NY - MAY 14: (L-R) Diane Sawyer, Caitlyn Jenner, and David Sloan attend the 27th Annual GLAAD Media Awards at Waldorf Astoria Hotel in New York on May 14, 2016 in New York City. (Photo by Bryan Bedder/Getty Images for GLAAD)
LOS ANGELES, CA - JUNE 10: Caitlyn Jenner is wearing a dress from Moschino seen before the Moschino Fashion Show in the streets of Downtown Los Angeles on June 10, 2016 in Los Angeles, California. (Photo by Timur Emek/Getty Images)
LOS ANGELES, CA - JUNE 10: Caitlyn Jenner (L) and singer Katy Perry attend the Moschino Spring/Summer 17 Menswear and Women's Resort Collection during MADE LA at L.A. Live Event Deck on June 10, 2016 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
MALIBU, CA - JULY 03: Caitlyn Jenner seen out for grocery shopping on July 03, 2016 in Malibu, California. PHOTOGRAPH BY Barcroft Images London-T:+44 207 033 1031 E:hello@barcroftmedia.com - New York-T:+1 212 796 2458 E:hello@barcroftusa.com - New Delhi-T:+91 11 4053 2429 E:hello@barcroftindia.com www.barcroftimages.com (Photo credit should read Barcroft Images / Barcroft Media via Getty Images)
LOS ANGELES, CA - JULY 13: TV personality Caitlyn Jenner attends the 2016 ESPYS at Microsoft Theater on July 13, 2016 in Los Angeles, California. (Photo by Kevin Mazur/Getty Images)
Republican transgender rights activist Caitlyn Jenner participates in a Big Tent Brunch organized by the American Unity Fund in Cleveland, Ohio, during the Republican National Convention, on July 20, 2016. / AFP / Ivan Couronne (Photo credit should read IVAN COURONNE/AFP/Getty Images)
LOS ANGELES, CA - JULY 21: Caitlyn Jenner is seen on July 21, 2016 in Los Angeles, California. (Photo by BG010/Bauer-Griffin/GC Images)
LOS ANGELES, CA - SEPTEMBER 14: Caitlyn Jenner is seen at LAX on September 14, 2016 in Los Angeles, California. (Photo by starzfly/Bauer-Griffin/GC Images)
LOS ANGELES, CA - AUGUST 19: Actress Candis Cayne and TV personality Caitlyn Jenner attend a cocktail reception Benefit for onePULSE Foundation at NeueHouse Hollywood on August 19, 2016 in Los Angeles, California. (Photo by Alberto E. Rodriguez/Getty Images)
LOS ANGELES, CA - OCTOBER 22: Caitlyn Jenner attends the 15th Annual Queen USA Transgender Beauty Pageant at The Theatre at Ace Hotel on October 22, 2016 in Los Angeles, California. (Photo by Vincent Sandoval/WireImage)
BEVERLY HILLS, CA - OCTOBER 24: Caitlyn Jenner attends the screening of Summit Entertainment's 'Hacksaw Ridge' at Samuel Goldwyn Theater on October 24, 2016 in Beverly Hills, California. (Photo by Tommaso Boddi/WireImage)
THOUSAND OAKS, CA - OCTOBER 27: Caitlyn Jenner plays a tee shot during practice for the PGA TOUR Champions PowerShares QQQ Championship at Sherwood Country Club on October 27, 2016 in Thousand Oaks, California. (Photo by Ryan Young/PGA TOUR)
LOS ANGELES, CA - NOVEMBER 14: TV personality Caitlyn Jenner attends Glamour Women Of The Year 2016 at NeueHouse Hollywood on November 14, 2016 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
MALIBU, CA - NOVEMBER 19: (L-R) Brandon Jenner, Caitlyn Jenner and Brody Jenner attend the Brandon Jenner Record Release Party For 'Burning Ground' on November 19, 2016 in Malibu, California. (Photo by Earl Gibson III/Getty Images)
LOS ANGELES, CA - JANUARY 07: Olympic athletes Caitlyn Jenner and Simone Biles attend Life is Good at GOLD MEETS GOLDEN Event at Equinox on January 7, 2017 in Los Angeles, California. (Photo by Emma McIntyre/Getty Images)
WEST HOLLYWOOD, CA - FEBRUARY 26: Caitlyn Jenner and Andreja Pejic arrive at the 25th Annual Elton John AIDS Foundation's Oscar viewing party held at The City of West Hollywood Park on February 26, 2017 in West Hollywood, California. (Photo by Michael Tran/FilmMagic)
BEVERLY HILLS, CA - FEBRUARY 26: Caitlyn Jenner attends the 2017 Vanity Fair Oscar Party Hosted by Graydon Carter at the Wallis Annenberg Center for the Performing Arts on February 26, 2017 in Beverly Hills, California. (Photo by C Flanigan/Getty Images)
RANCHO MIRAGE, CA - MARCH 29: Caitlyn Jenner walks across the fairway of the 9th during the ANA Inspiration Pro-Am at Mission Hills Country Club on March 29, 2017 in Rancho Mirage, California. (Photo by Kelly Kline/Getty Images)
BEVERLY HILLS, CA - APRIL 01: TV personality Caitlyn Jenner (L) and Paris Jackson attend the 28th Annual GLAAD Media Awards in LA at The Beverly Hilton Hotel on April 1, 2017 in Beverly Hills, California. (Photo by Todd Williamson/Getty Images for GLAAD)
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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."

PICS: Caitlyn Jenner's Best Looks

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."

WATCH: Caitlyn Jenner Reveals Her 'Tipping Point' For Coming Out as Transgender

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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