Pushing Tin
(1999)

Connie (Cate Blanchett) leaves Nick (John Cusack) after finding out he cheated on her. A bomb scare happens at work and everyone evacuates. Nick and Russell (Billy Bob Thorton) stay to guide the remaining planes back home. Nick ends up leaving because the place was going to blow up but Russell stays, making him a hero that guided the final plane home. The bomb turns out to be a hoax and Russell quits and moves to Colorado with Mary (Angelina Jolie). Distraught, Nick tracks him down and confronts him about how his life sucks. They make amends and Russell helps him out in his own strange way.

Connie is on a plane home, planning on starting a new life, when she's called to the cockpit and Nick asks her out and apologizes to her through the radio. After serenading her with a song, she accepts.

Thanks Eric E!