The Beat Generation is known as one of the most polarizing, yet influential literary and cultural movements in American history. Writers like Allen Ginsberg, Jack Kerouac, and William S. Burroughs saw the world in a different light than what the media and mainstream society presented it. They embraced topics which were considered obscene or taboo at the time and demystified them in their works, giving the readers a glimpse of a different way of life. They were constantly criticized and were seen as outsiders, which is not surprising considering their avant-garde lifestyle of travelling and the constant search for “the kicks.” They were an underground group of writers and artists that all shared the same ideas and visions, as well as a detest for the materialistic society and the censorship present in the media. After their most known releases, Kerouac’s On the Road in 1957, Ginsberg’s Howl in 1956, and Burroughs’s Naked Lunch in 1959, the Beats gained a wider audience. They became pop culture icons, which the media recognized and used for their own financial profit. Their influence was also visible in music and cinematography, further cementing their legacy. Decades later, the Beats became what they fought against – a part of the mainstream culture and materialism appearing on the covers of fashion magazines and advertisement for multi-million-dollar companies. While the people behind the movement changed, their foundational ideas still exist and continue to inspire young people worldwide. This paper aims to portray the Beat Generation in the context of the post-war America, explain the importance of the movement on a number of examples, as well as examine the influence of Beat literature on popular culture and its lasting legacy.