Spectroscopic analyses of Type Ia supernovae have shown there exist four spectroscopic groups---cools, broad line, shallow silicon, and core normal---defined by the widths of the Si II features at 5972 Angstroms and 6355 Angstroms. 1991bg-likes are classified as cools. Cools are dim, undergo a rapid decline in luminosity, and produce significantly less nickel than normal Type Ia supernovae. They also have an unusually deep and wide trough in their spectra around 4200 Angstroms and a relatively strong Si II absorption attributed to the line at 5972 Angstroms. We examine the spectra of supernova (SN) 1991bg and the cools SN 1997cn, SN 1999by, and SN 2005bl using the highly parameterized synthetic spectrum code SYNOW, and find general agreement with similar spectroscopic studies. Our analysis reveals that this group of supernovae is fairly homogeneous, with many of the blue spectral features well fit by Fe II. The nature of the spectroscopic commonalities and the variations in the class are discussed. Finally, we examine intermediates such as SN 2004eo and discuss the spectroscopic subgroup distribution of Type Ia supernovae.