While studying economics at UCLA, Solomon developed two very important working relationships--one with Chris Matheson, with whom he would later co-write "Bill & Ted's Excellent Adventure" and its sequel "Bill & Ted's Bogus Journey" (1991), the other with a young comedian named Garry Shandling. Solomon's association with that performer led to his appointment as executive story editor on Showtime's highly acclaimed series "It's Garry Shandling's Show".
Solomon started his career selling jokes to Shandling and other comedians and writing plays. Upon leaving UCLA, he toured the country as a stand-up comedian and at the age of 21 joined the writing staff of the popular ABC sitcom "Laverne & Shirley" in the early 1980s. After his stint with "It's Garry Shandling's Show" in the mid- to late-1980s, Solomon and Matheson decided to try to bring to the big screen a pair of characters they had created in a college improv group. The writers sold their script and teenagers and young adults everywhere flocked to theaters to watch "Bill & Ted's Excellent Adventure", a light-hearted romp featuring two California dudes (played by heartthrobs Keanu Reeves and Alex Winter) traveling through time. Solomon and Matheson reunited in 1991 for the charming, yet less successful sequel "Bill & Ted's Bogus Journey", which the writers also co-produced. Solomon followed that effort up with screenplays for the poorly received "Leaving Normal" (1992) and "Super Mario Bros." (1993). He hit pay dirt in 1995, however, when he penned the script for the blockbuster summer movie "Men in Black", which was based on the Malibu comic book series and starred Tommy Lee Jones and Will Smith. Seemingly most comfortable and successful crafting fantasy-themed comedies, the screenwriter made a foray into darker territory in 2000 when he co-wrote the script for "X-Men", another feature film based on a comic book series. That same year he also lent his talents to the Garry Shandling turkey "What Planet Are You From?" and the feature film production of "Charlie's Angels".