years later. Career Origins For eight years following grad school, Simmons lived in Charlestown working various jobs before eventually landing a job at ESPN. The September after grad school, Simmons started working at the Boston Herald as a high school sports reporter and editorial assistant, mainly "answering phones... organizing food runs, [and] working on the Sunday football scores section." Three years later he got a job as a freelancer for Boston Phoenix but was broke within three months and started bartending. In 1997, unable to get a newspaper job, Simmons "badgered" Digital City Boston of AOL into giving him a column, and he started the web site BostonSportsGuy.com while working as a bartender and waiter at night. He decided to call his column "Sports Guy" since the site had a "Movie Guy." Originally the column was only available on AOL, and Simmons forwarded the column to his friends. He began receiving e-mails from people asking if they could be put on his mailing list. For the first 18 months, Simmons would send it to about 100 people, until it became available on the web in November 1998. The website quickly built up a reputation as many of Simmons' friends from high school and college were e-mailing it to each other. In 2001, his website averaged 10,000 readers and 45,000 hits per day. Jimmy Kimmel Live! In the summer of 2002, Jimmy Kimmel had been trying to get Simmons to write for his new late-night talk show, Jimmy Kimmel Live! which was to premiere after the Super Bowl. Simmons refused for most of the summer because he did not want to cut back on his columns and move to the West Coast away from his family and Boston teams. Kimmel kept on "badgering" him and by mid-September Kimmel had him "on the ropes." It was crucial for Simmons that he could write for the show and on ESPN.com and in ESPN The Magazine, which was possible because of the Disney connection with ESPN and ABC. He has also stated that he joined the show because he was burned out from his column, felt he needed a change, and always wanted to write for a talk show. Simmons left Boston and moved to California on November 16, 2002 and began working in April 2003 as a comedy writer for the show. Simmons called it "the best move I ever made" and said