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"Head Like A Hole" is the first track on the 1989 release Pretty Hate Machine. It was the first commercial success Trent Reznor had and received wide radio rotation at the time. Though Reznor doesn't dislike the song, he was quite surprised it became as big as it did, especially due to its relatively easy writing process compared to some of the lesser recognized tracks on Pretty Hate Machine ("That's What I Get" and "Kinda I Want To" most notably.)

The version that appears as the first track on Pretty Hate Machine, it's perhaps one of the most well known Nine Inch Nails songs. Its pounding synth bassline, tribal rhythms and chants, layered guitar and catchy double chorus are all signature aspects of the song. The stereo wipe at the end fades into the beginning of "Terrible Lie." The tribal chants are sampled from "Samburu Warriors' Initiation (Kenya)" taken from field recordings under the title East Africa Ceremonial & Folk Music (performed by the Samburu Tribe of Kenya and recorded by David Fanshawe.) There is a sample from 3:12 to 3:19, first appearing in the right channel and then the left, that may be a saxophone.

In a 2005 interview with Kerrang, Reznor gave the following insight: "I don't remember what I was thinking about at the time, but it was pretty much about yelling at a beast without putting a face to it. I wrote it at the last minute as a throwaway. The rest of Pretty Hate Machine was already written, and we'd revised everything else about nine times. Up until then song-writing had been a meticulous and agonising process, but this took me 15 minutes in my bedroom. The fact that it produced this huge reaction really pissed me off because I hadn't agonised over it. I was still back in Cleveland, and I had a job working at a studio where I'd spend time at night learning how to record and engineer things and I tried to work out how my voice sounded. I was playing everything myself but I had no confidence in playing guitar. I was convinced that if any real players heard it they'd laugh. Now I know that's bullshit but at the time I was very insecure."

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