Originally from Virginia, Rawlings received his B.A. with honors in classics from Haverford College in 1966. From there he moved to Princeton University, where he received a Ph.D. in classics in 1970. After graduating from Princeton, he joined the faculty at the University of Colorado at Boulder, rising to full professor in 1980. Rawlings began his career in academic administration at Colorado, serving as chairman of the classics department and later as associate vice chancellor for instruction. In 1988, Rawlings was named President of the University of Iowa, a position he held until 1995.
Rawlings then came to Cornell University, becoming its 10th president, serving from 1995 until 2003. At Cornell, he was an effective fundraiser, presiding over several large capital campaigns. Rawlings created several new positions and programs to support undergraduate education, began the construction of several new dormitories, centralized the location of freshmen on campus (initially protested by Al Sharpton and others due to alleged racial implications), and promoted stronger undergraduate admissions standards. Rawlings began initiatives in certain areas of science and engineering that he considered especially important to the future (such as bioinformatics, computational biology, computer and information sciences, genomics, and materials science), and began plans for a large new life sciences building. He encouraged interdisciplinary exchanges in the humanities and social sciences. He also presided over an agreement to establish a branch of Cornell's medical school in Qatar, the Weill Cornell Medical College in Qatar.
While President of Cornell, Rawlings also held the rank of professor of classics, and continued to hold this position after he left the presidency. Notably, during the last two years of his presidency, he taught an undergraduate course in classics. At the same time, Rawlings faced criticism from many students and alumni leaders for his hands-off approach toward the student body and his focus on the business operations of Cornell.
After the sudden resignation of his successor as president, Jeffrey Lehman, effective June 30, 2005, Rawlings agreed to reassume the presidency on an interim basis until a permanent replacement could be found. On January 21, 2006, David J. Skorton was announced as the next president of Cornell. Skorton took office on July 1. (Like Rawlings, Skorton was previously President of the University of Iowa.)
Currently, he serves a professor of classical history in Cornell's Department of History and Department of Classics.