The Expendables | 1999
A top-secret operation is authorized to rescue an undercover agent from a dangerous Cuban jail, where she is being terrorized to divulge classified information. Six women, all violent felons being held in a maximum-security prison with no hope of ever being paroled, are presented with the opportunity of obtaining their freedom in exchange for their participation in this mission. The women are released to the custody of Colonel Finley Deacon. and are put through regimented "boot camp" training before the rescue mission -- which involves trekking through the Cuban jungle to reach the jail.
A small fishing boat transports Deacon and the inmates into Cuba. Upon arrival, they disguise themselves as Cuban prostitutes while Colonel Deacon and Vera Cortez disguise themselves as Cuban police who have arrested them. After reaching the prison where the American advisor is being held, the group attempts to get her out safely. Not, however, before a gunfight ensues, leaving the crew running for their lives. Once they reach what they perceive as relative safety, the women realize that the real danger is yet to come when Nicoline Chatoris reveals herself as an undercover CIA agent sent to contain the mission via termination. Nicoline manages to inflict a fatal shot into Deacon before she herself is gunned down by the Cuban police. The rest of the inmates successfully make it to safety with the American agent in tow. The remaining inmates are granted their freedom once they arrive back on American soil.