Singer Pat Monahan said the song "was just a gag about a girl breaking up with a boy and being just so immature that the only way to handle it was just to tell your friends that she's dead.

"[2] The lyrics are a tongue-in-cheek narrative where to save face, the singer claims he will say his girlfriend died in a variety of outlandish ways rather than admit she dumped him.

Nick Bassett of The Re-View compared "50 Ways to Say Goodbye" to its predecessor, saying that "whilst it lacks that Summery carefree vibe [of "Drive By"], this newbie is still buoyed by a jaunty radio-friendly chorus".

[4] The music video was directed by Marc Klasfeld and features David Hasselhoff, Taryn Manning, Jonathan Lipnicki, and a Mariachi trio, in addition to band members Pat Monahan, Jimmy Stafford, and Scott Underwood (Stafford and Underwood have since left the band).

At the end of the video, Pat's girlfriend is revealed to be alive and says hello to him and Hasselhoff, who stand awkwardly as she continues her shopping.