Established in 1979, IML is held annually in Chicago over Memorial Day weekend, drawing thousands of contestants and spectators from around the world.

[4] The "Mr. Gold Coast" contest became one of the bar's most popular promotions causing the need to locate the competition to a larger venue in 1979, upon which the title was changed to International Mr.

[5] The event was advertised as "a weekend you won't want to miss" featuring "some of the world's hottest men, representing leather bars and clubs across America and Europe" competing to win prizes worth $5,000 ($21,662 in 2024), including a motorcycle.

[5] Spectators could purchase a weekend package for $25 ($108.00 in 2024) that included a shirt designed Etienne (Orejudos), tickets to parties and events, and coupons for local shops and bathhouses.

[72][73] In 2010, Tyler McCormick became the first openly transgender man, the first wheelchair user, and the first person from New Mexico to win International Mr.

[34] His win also marked the first time black men won consecutive International Mr. Leather titles.

The bootblack contestants work during the Friday, Saturday, and Sunday of IML during the time that the Leather Market is open, a total of approximately 20 hours over three days.

In previous years, the bootblacks were allowed to shine boots and collect tickets at all times during the weekend.

This agreement was conceived to give the contestants the freedom to take time to enjoy the weekend without feeling the pressure to always be bootblacking.

This change was made largely because it was commonly held that women had a significant disadvantage competing for ballots from IML's predominantly gay male attendees, who may favor bootblacks who they find attractive.

The winner of the International Mr. Bootblack Competition is announced (along with the first and second runners-up and the winner of the Brotherhood Award, on which the IMrBB competitors vote and which is roughly analogous to the Miss Congeniality Award from various traditional beauty contests) at the Sunday contest, immediately following the announcement of the top 20 IML finalists.

An IMrBB party is held in a hotel function room on Saturday night, offering food, music, and a silent auction, the proceeds of which go to the travel fund of the winner.

These sources of revenue have provided the various contestants with significantly more money to aid their travel to distant events during their title years.

The money is controlled by the contest coordinator, and any access to the funds must be accompanied by proof of the travel outlay.

[11] The following is a table of IMrBB contest winners:[12] According to the Chicago Reader in 2024, "IML has endured as an institution that serves the LGBTQ+ community by fundraising for grassroots groups as well as providing opportunities to gather and exchange goods, information, and kinship.

[78] The Leather Archives & Museum’s photos, videos, and oral histories chronicling IML (and International Ms. Leather) were featured in a 2015 documentary by Christina Court, titled High Shine: 15 Years of International Ms Bootblack.