on the road first
on the road has to be read first. the dharma bums may not even be a good second choice. it was written quickly after road was published to cash in on the beat fame. on the road was his first try at his new style so it makes sense to read him kind of in order of his progression. other books written before road was published include maggie cassidy, the subterraneans, tristessa, mexico city blues and visions of cody. anyways, on the road begins in the late 1940's with a young unknown kerouac developing a new style whereas dharma bums takes place in middle fifties written at the peak of his fame. if i remember correctly he even uses regular punctuation and not his speed dashes. in bums he goes full on into buddhism and it's better to lead up to that with his other books. just my opinion.