The 25th anniversary…. Midwest Awards Ball presents POP CULTURE ICONS: I ❤️ The 90s!
Schedule
Sat, 25 Apr, 2026 at 05:00 pm to Sun, 26 Apr, 2026 at 02:00 am
UTC-05:00Location
The Grand Ballroom Chicago | Chicago, IL
The 25th anniversary….Midwest Awards Ball presents
POP CULTURE ICONS:
I ❤️ The 90s!
Saturday April 25, 2026
Chicago, IL
Ballroom Kingdom
6351 S. Cottage Grove
Doors: 5pm Awards 6pm LSS 6:45 Showtime 7pm SHARP!!!
“Honoring the stars of today, the statements of tomorrow and the forever Legends and Icons”…..
Entry $40 all night (no Zelle, Venmo, ApplyPay). Cash only!!
VIP no line, no wait $60
Cash bar $$$
Tables goes on sale 12/15/2025; Exclusive, Premium, VIP, and General
Grandprizes:
$1K Geoffrey Butler (Fresh Prince of Bel-Air) – Executive Realness
“Witty and sharp, always dressed to impress, Tailored to perfection, no wrinkle, no mess.
Keep that mansion in order, your presence in place—A thousand on the line, now serve butler grace!”
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$1K The Bizarre Bizarre – Unconventional, Pop & 90’s Flair
“Unleash your mind, let your bizarre thoughts ignite, Mix pop culture, fashion, with a 90’s delight. From street to chic, make the crowd stare—Your bizarre creation must slay with flair!”
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$1K Women’s Face – 90’s Phyne and Divine
“Phyne in the 90’s, a minimal dream, Halle, Nia, Janet—the glow, the gleam. Bring that picture, oversized for the space,
So we all can praise your flawless face!”
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$1K OTA Performance – In Living Color “1990 brought laughs and dares, The Wayans showed talent from everywhere. Vogue Fems—Blaine Edwards & Antione Merriweather’s pride;
Twisters—Fire Marshall Bill wild side; BQID—Wanda funny faces and all; FQ—Fly Girl, serving body and honey; Old Way—Homey the Clown, don’t play. $1K on the line—serve, slay, and stay!”
Tables are on sale NOW!
Pop Culture Icons: I Love the 90’s — Full Category List:
OTA Categories
New Face:
Colorful mug, comp card clean—90’s fresh, camera keen.
New Runway:
“Tyra Mail” walk—top model talk. In all black, don’t get packed.
New Vogue:
TRL pop-star tease—your favorite artist graphic tee, crowd on freeze.
Best Dressed:
VH1 Vogue Fashion awards flair—red carpet look, speech prepared.
Glitz & Glam:
Sequins, pads, bodice bold—90’s pageant, glam in gold.
High Fashion Streetwear:
Archive drip, vintage fame—Phat Farm, Enyce, Karl Kani fly, still got game.
Sneaker vs Sneaker:
Retro kicks, classic heat—90’s soles that still hit the streets.
Old Way:
Kangol low, shell toes dip—Adidas track suit, with that classic grip.
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Women’s Categories
Women’s Body:
MTV Spring Break body—two-piece, heels, body on oody.
Women’s Runway:
Victoria’s Secret soar—lingerie, wings, unstoppable walk on the floor.
Women’s Performance:
Madonna Vogue video tryout—oversized suit, pose it out.
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Transman & Butch Categories
Butch & Transman Realness (2 trophies):
Airbrush fits, denim flow—90’s cool, let it show.
Transman Sexy Face:
Smooth and fly, quiet flame—90’s charm, and they’ll remember your name. (In all red)
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BQ Categories
BQ Face:
Calvin Klein’s muse, mug supreme—white tee, classic fit jeans, such a 90’s dream.
RWT:
Urkel nerd to prom-night clean—switch it up, serve both scenes. Part 1: Steve Urkel. Part 2: Stephon Urkel
BQ PrettyBoy Realness:
Boyz N the Hood attire—snapbacks, jerseys, street desire.
BQ Thug Realness:
Baggy fits, Timbs, leathers real
tight—90’s hip-hop era, could it be your night?
BQ SchoolBoy Realness:
Carlton Banks prep or Will’s wit—be Bel-Air fly, make your best pick.
BQ Body:
WWF shorts, boots on smash—ring-ready, body built to clash.
BQ Everyday Realness:
Tommy down, Nautica fine—head-to-toe 90’s phyne. In H2T Tommy Hilfiger, Polo Ralph Lauren or Nautica gear.
BQ Sex Siren:
Before the apps, late-night screen—HBO tease, Cinemax dream.
BQ European Runway:
Denim stacked, plaid on slayy—high fashion chic, it’s the “Clueless” way.
BQ All American:
TLC “Creep” casting scene—silk pajamas, smooth and clean.
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FQ Categories
FQ Sex Siren:
Queen Bee reign, bold and raw—Lil’ Kim tease, must be iconic—that’s law.
FQ Runway:
“Queen of the Night” ignite—Whitney Houston’s Bodyguard glam, own the light.
FQ Body:
BET Uncut, after dark—Tip Drill tease, leave your mark. The look is all up to U.
FQ Realness:
Moesha’s the mood, cool and fly—90’s style of girl, walk on by.
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Drag Categories
BQID Runway:
Where is it happening?
The Grand Ballroom Chicago, 6351 S Cottage Grove Ave,Chicago, Illinois, United States
Know what’s Happening Next — before everyone else does.
