Bellows was an urban realist, a second-generational heir to the Ashcan School of Arthur Davies, John Sloan and of course Henri. He painted street brawls, tenement children swimming off the docks, and the proverbial "huddled masses". But Bellows had the versatility to, in a sense "have it both ways". He also painted elegant high society scenes, the beautiful people of the time playing tennis, watching polo, fashionably dressed, and living the "good life". Like many of his forebears he was a very macho "man's painter", his up-close and personal paintings of then-illegal prize fights such as Both Members of This Club and Stag at Sharkey's being perhaps the best known works of his career.

Like his subject manner, Bellows brushwork was termed "zestful". Brutal might be a better word. It might also be described as brusque and rough. Though no stranger to the country club set, Bellows also had a social conscious. His urban landscape entitled Cliff Dwellers, painted in 1913 depicts some of the worst of New York City's ghettoes in the midst of a heat wave, the suffering masses almost literally melting into the streets from the open windows and fire escapes of their tenement slums. One can almost hear the noisy children and the harsh sounds of many different of languages all crying out for some form of relief, not just from the heat but from the dreariness of their lives. But just as Bellow's painting subjects ran on both sides of the tracks, so did his career. He was both a participant in the radical 1913 Armory Show and in the same year was elected to full membership in the conservative National Academy of Design. Like his heavy-handed handling of paint, he also turned "having it both ways" into something of a fine art.