After graduating from Northwestern University's Medill School of Journalism in 1978, Friendly became a journalist, a staff writer at newsmagazine Newsweek.

[1] He moved to the Los Angeles Times in 1985 where he wrote about the entertainment industry and had a weekly column exploring the business side of the film industry until 1987,[2] when he was approached by Imagine Entertainment co-founders Brian Grazer and Ron Howard, and he became Imagine's Vice President of Motion Pictures.

[1] Friendly and producer/financier Marc Turtletaub founded Deep River Productions in September 2000 and,[3] after working at 20th Century Fox for three years where he produced Big Momma's House, they produced their first feature, Laws of Attraction.

[4][5] After the release of Little Miss Sunshine, which had been in production at Deep River Productions for six years,[2] Friendly and Turtletaub split and left the company to work elsewhere and Friendly made a two-year producing deal with 20th Century Fox that landed him producing roles on the 2008 film Meet Dave and Big Mommas: Like Father, Like Son.

[4] He is also set to produce the upcoming projects Office Romance, Q School, and The Warden.