Archive · Winning Wednesdays + Headlinerz
Winning Wednesdays Archive
The receipts behind the legacy
This archive preserves selected flyers, photographs, videos, and promotional materials from Winning Wednesdays and other Headlinerz events. Together, these materials document years of independent artist showcases, competitions, live events, radio opportunities, cash prizes, media exposure, and artist development.
These materials are presented as historical records of the work that helped shape the philosophy behind Headlinerz International today.
Read the Winning Wednesdays storyArtist competitions & prizes
Competition flyers and photographs of cash prizes being presented, from Winning Wednesdays nights.
$500 competition · Aug. 29, 2012Rap, R&B and comedian competition at Adrianna’s, with judges and sign-up hours listed. 
$500 grand prizeFirst place $500; second place an interview and song on Power 92 RawTV Radio, as advertised at the time. 
Holiday edition · 12/12/12Best performance received $250 plus a gift card, as advertised.
Radio & media
Flyers and promotion that advertised radio play, spins and interviews.
Radio prizes · Wed., Dec. 26A month of spins on BandKamp Radio plus an on-air interview for first place, as advertised. 
Weekly prizesA Headlinerz Entertainment flyer listing weekly cash and studio-time prizes and interviews with radio play.
Live events & crowds
The room, the audience and the venue.
Adrianna’sThe home of Winning Wednesdays. 
Venue marqueeThe Adrianna’s sign advertising Winning Wednesdays as the “#1 Open Mic.”
Winning Wednesdays flyers
Promotional flyers across different weeks, themes, hosts, judges and sponsors. Sponsor branding reflects the time and does not indicate a current partnership.
Every WednesdayRegistration and show times, with a free performance slot for artists who brought five or more supporters. 
Every Wednesday at Adrianna’sA weekly flyer listing live performers and an open artist sign-up. 
Performance battleA sponsored performance-battle flyer with first-come registration. 
April 18A Headlinerz Ent. flyer with special performances and artist sign-up before the show. 
Legacy team competitionAn all-genre team competition judged on crowd reaction, as described on the flyer. 
Aquarius BashA themed Winning Wednesdays night listing R&B, poetry and rap performances.
Headlinerz events
Other Headlinerz-branded events from the same period. These were not Winning Wednesdays nights.
A Taste of Chicago · April 3, 2012Headlinerz Ent presents a concert night at The Ultra Lounge. 
A Taste of Chicago 2 · March 23Headlinerz presents a concert at The Rap Factory. 
Eye Candy in Exotic Stilettos · Nov. 27, 2011An all-female concert and model meet-and-greet presented by Headlinerz Ent. 
Strut Yo Stuff · Feb. 13A fashion show presented by Headlinerz Ent and 3230 Ent at Adrianna’s. 
Social Club Sundays · July 31, 2011Headlinerz Ent presents a Sunday night for bike, car and social clubs. 
Battle on the Ave · Feb. 8An event flyer carrying the Headlinerz mark. 
Turn Up TuesdaysA weekly hip hop showcase flyer carrying the Headlinerz logo, with artist sign-up.
Fokus + Beuller
Fokus Da Konnect and Beuller The Gaud hosting at Winning Wednesdays.
Video archive
Archival video, played only when you press play.
The prize was real
Radio opportunity in action
Personal phone numbers printed on some archival flyers have been blurred. Flyers are shown as historical event material from the time.
Headlinerz International