"Terrible place, isn't it," said Tom, exchanging a frown with Doctor Eckleburg.
Chapter 2 · Tom Buchanan
Context
While waiting for Myrtle down the road from Wilson's garage, Tom comments on the valley of ashes to Nick.
Analysis
The phrase 'exchanging a frown with Doctor Eckleburg' personifies the billboard as a sentient being capable of social interaction with Tom, creating a surreal moment in which a symbol of moral oversight appears to engage in casual conversation. Tom's dismissal of the valley as merely 'terrible' reveals his inability to recognize his own complicity in the system that produces such wastelands. The irony is rich: Tom condemns the environment while exploiting its most vulnerable inhabitant.
How to Use in Essay
Effective for essays on the Eckleburg eyes as moral symbol, Tom's hypocrisy and lack of self-awareness, or the relationship between wealth and the waste it produces.