Horrible Bosses was released on July 8 , 2011 in the United States and Canada across 3 @,@ 040 theaters . It grossed $ 9.9M on the first day , giving it the second largest opening gross for an original R @-@ rated comedy of the summer , behind Bad Teacher ( $ 12.2M ) . For the opening weekend , the film took in a total of $ 28 @,@ 302 @,@ 165 , an average of $ 9 @,@ 310 per theater , making it the number two film for the weekend , behind Transformers : Dark of the Moon ( $ 47.1M ) , the second highest @-@ grossing opening weekend for an original R @-@ rated comedy , again behind Bad Teacher ( $ 31.6M ) , and the highest @-@ grossing opening weekend ever for a dark / black comedy film , overtaking the 2004 The Stepford Wives ( $ 21.4M ) . The opening weekend audience was 51 % male , and 64 % of the audience were over 25 years of age . The second weekend ( 15 – 17 July ) saw a further 94 theaters added , for a total of 3 @,@ 134 . Box office revenue dropped by a " respectable " 38 % , taking $ 17.6M for a total gross of $ 60M in ten days . The film ranked third for the weekend . It remained in the top five films during its third week , dropping 33 % and leaving thirty theaters from the previous weekend , to take in $ 11.9M for a gross of $ 82.6M in 17 days . On July 28 , 2011 , with $ 87.6M after 20 days , Horrible Bosses surpassed The War of the Roses ( $ 86.8M ) to become the highest grossing dark / black comedy film in unadjusted dollars .