Any reader of Tobias Smollett’s novel Humphry Clinker will notice that, during the expedition, humor seems to exist more consistently and with greater frequency in the sections devoted to England in comparison to the more earnest and serious sections devoted to travel in Scotland. I will argue that Humphry Clinker stands as a brilliant example of literary insurgency. Smollett is crafty in his use of devices to force readers to take on his own views without realizing they have. Smollett has a point to make, that Scotland is a worthy northern neighbor to England with something to offer, and he uses every tool of engagement available to him in order to present his personal beliefs about Scotland to a prejudiced English audience. This is an audience long fed, by the likes of Samuel Johnson, that Scotland is a savage land full of uncivilized people and a complete lack of culture. No reader can walk away from Humphry Clinker without a favorable view of an under-appreciated, charming nation full of entrepreneurism, industry, and a strong moral foundation. The ways in which Smollett engages his unsuspecting readers so that they will also invest in his pro-Scotland ideals are his use of the epistolary form and the codified use of humor along class lines. This thesis seeks to build a taxonomy of the humor used in the novel to understand how Smollett reveals class as a weapon in converting readers. An examination of the formidable power of the epistolary form will also underscore the importance of reader engagement with multiple perspectives and nuanced layers of understanding. We will see how, with his final novel, completed just before his death, Smollett creates a work of genius that builds a new, more positive vision of Scotland against the deep prejudices of its southern neighbor.