Berry graduated from Syracuse University in 1992 with a degree in Electronic Media.

After graduation, Berry moved to Los Angeles to work in show Business. After a few odd jobs Berry got hired as a production assistant for The George Carlin Show on Fox. Berry worked on the show for one year and has fond memories of George Carlin who wrote a recommendation letter for the Warner Brothers Writer's Workshop. Thanks in part to the recommendation, Berry was accepted to the workshop, officially getting him into the LA writing scene. During his writing tenure, he worked on such movies as Crocodile Dundee in Los Angeles, and the final year of the TV show Married... with Children. Crocodile Dundee was nominated for a Razzie award in 2001 under the category of "Worst Remake or Sequel", but lost to Planet of the Apes. Berry gained further (possibly unwanted) attention for Crocodile Dundee in Los Angeles after Paul Hogan filed a lawsuit against Berry and the Writer’s Guild of America because Berry and Eric Abrams were credited as Writers, while Hogan insisted that he was the only one who wrote it. Berry and Abrams maintained their writing credits.

Berry began his first foray into audio podcasting in 2007 with the “Fantasy Forget (Four Get)” where he gave “four players to leave off your roster this week.” In June 2007, Berry and fellow ESPN fantasy analyst Nate Ravitz were announced as the full-time hosts of the Fantasy Focus Baseball Podcast and, soon after, the Fantasy Focus Football Podcast. Ravitz was replaced in 2015 by Field Yates. The shows are produced by Daniel Dopp and have featured many recurring ESPN guests such as Stephania Bell, Mike Clay, and Tristan Cockcroft. Currently Mathew Berry owes co-worker Field Yates a one-year membership of Blue Apron as compensation for the infamous Bolden Pryor trade of 2016. This debt has been settled (10/20/16).

The Fantasy Focus Football podcast is ESPN's most downloaded original-content podcast (and second overall behind only the podcast version of Pardon the Interruption). It consistently ranks among the top ten podcasts on iTunes and in August 2009, was the #1 audio podcast on all of iTunes. The show has won a total of five awards from PodcastAwards.com, including "Best Sports Podcast" in 2009, 2011, and 2012, and the overall "People's Choice" podcast in 2009 and 2012.

Berry’s Sports team allegiances lie from coast to coast. He is a Texas A&M fan because of his close familial ties with the program, having season tickets in his youth. Due to his residences in Virginia, Berry’s favorite NFL team became the Washington Redskins. During his time in Los Angeles, Berry gained an affinity for the Los Angeles Angels, and Los Angeles Lakers. As of October 27, 2010, Berry has adopted a support for the London-based football club West Ham United F.C..

Berry initially wrote two main fantasy columns for ESPN, "The Talented Mr. Roto" and "TRUM: Thoughts, Ramblings, Useless Info and Musings". However, his last post on the TRUM blog post was written in October 2011.

Berry announced on the last episode of the 2013 Fantasy Focus Baseball Podcast that he would not return to host the podcast for the 2014 season. This was announced immediately after Nate Ravitz announced his departure from the show.

Currently, Matthew Berry writes a number of larger fantasy articles annually for what is now known as ESPN’s Fantasy Football Draft Kit. First, there is “100 Facts”, which is both printed in ESPN The Magazine and posted on ESPN.com. Second is the “Draft Day Manifesto,” where he goes over basic and advanced stats and tips to help ensure you succeed in your draft without necessarily recommending certain players. Third is Berry’s pre-draft Love/Hate. Love/Hate focuses on players who he feels are being over or under drafted. He originally wrote Love/Hate, 100 Facts, and a Bold Predictions column for Fantasy baseball as well, but penned his final editions of these in 2014 to focus on football.