Jennifer Coolidge burst onto the scenes in the late 1999s when she appeared in American Pie as the infamous Jeanine Stifler, aka "Stifler's mom," and in Legally Blonde as the hilarious Paulette Bonafonté. However, as a report from The Things revealed, she actually started working in the industry several years prior in 1993.
At that time, the now-59-year-old was just 32 and appeared to have trouble getting major roles. But, rather than give up, Coolidge staged focused and ultimately saw success.