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"Looking Down the Barrel of a Gun" is the 10th track on the album Paul's Boutique by American hip hop group the Beastie Boys, released on July 25, 1989.

* Produced & written by the Beastie Boys and the Dust Brothers.
* Engineered by Mario Caldato & Allen Abrahamson.

The track contains the most live instrumentation on Paul's Boutique, with guitar and bass played by Adam Horovitz and Adam Yauch respectively.

The song was later covered by the band Anthrax for the 1993 compilation album The Beavis and Butt-Head Experience.

The lyrics "Get hip don't slip knuckle heads/Racism is schism on the serious tip" were repeated in the Sublime song "Don't Push."
Songs sampled

* "Time" by Pink Floyd
* "Mississippi Queen" by Mountain
* "Last Bongo in Belgium" by the Incredible Bongo Band
* "Put Your Hand in the Hand" by Ocean
Popular culture references

* John Rambo ("Rapid Fire Louie, like Rambo got bullets")
* A Clockwork Orange
* Die Hard ("I'ma Die Harder like my kid Bruce Willis")
* Bruce Willis
* David Berkowitz ("You got your finger on the trigger like the Son of Sam")

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