Self-destructive behavior
The majority of the poem consists of the choral "We" listing the various vices in which they engage, implying a link between the performance of "coolness" and vice which ultimately leads to misfortune.
The first stanza, "We real cool. We / Left school. ..." implies a direct correlation between truancy or dropping out and "coolness," or being hip, admired, and respected by one's peers. This also places coolness in direct opposition to institutions and power structures like the education system.
The pool hall's name, "Golden Shovel," underscores the notion that these young men are "digging their own graves" with their gilded displays of resistance. In other words, the shovel with which they dig their own graves is "golden" because their vices make them feel good and cool in the moment. Drinking gin, playing pool, and staying out late are displays of independence and hedonism; but the final line demonstrates that these players understand that while these may be their golden years, they are nonetheless driving them to their graves.
Masculinity
Though there is nothing in the poem to tell the reader explicitly that all seven pool players are young men, we can contextualize the poem in the time it was written and know that women rarely stepped into pool halls, let alone played pool. If historical context isn't enough, we can take Brooks' own word for it; she has said in interviews about the poem and in speaking about the inspiration behind the poem that she was writing about a group of young men in her community.
Coolness relates to the concept of masculinity, in this case, the masculinity of young, Black men in urban settings, in the sense that they are both performances which demonstrate resilience in the face of institutionally imposed adversity. Brooks has said that when she encountered the group of boys playing pool during school hours, she resisted judgment and instead tried to think about how they felt about themselves.
However, emotion and self-examination are often thought to diametrically oppose what it means to be "masculine," especially in oppressive conditions when "coolness" is characterized by not feeling and instead accepting one's lot in life with an unreadable poker face.
Brooks ingeniously accesses her characters' vulnerability while maintaining their front of "coolness." Instead of showing the young men explicitly question their own externality, instead of having the young men wonder if the community perceives them as "cool," she has them state it as a fact. But the line "We real cool" can be read as a desperate attempt to convince oneself of something instead of a confident declaration.
