MYB transcription factors (TFs) serve many important regulatory roles in plants, making them an important topic of study. However, like many large gene families, there are many inherent difficulties in understanding both the individual roles, and evolutionary history of MYB TFs. Individually, it may be difficult to isolate the functions of a given MYB TF, as there are numerous similar TFs serving related or overlapping functions. As a group, the similarities between members of a gene family can make it difficult to disentangle the forces causing their propagation and maintenance. There are many essential pathways governed by TFs that have evolved via massive expansions, such that a high degree of similarity and redundancy occurs within the gene family. This thesis is concerned with confronting this complex issue, attempting to learn as much as possible about the history and patterns found within the MYB TF family. The objectives of this research are to examine the results of screens involving MYB TF binding partners, and to apply new tools and methods to MYB genes to learn about their evolutionary history. Based on the meta-analysis of biological screens and the use of phylogenetic and recombination detection techniques, this research proposes mechanisms to explain patterns observed and improve the predictive power of computational approaches.