Rakoff won his battle with Hodgkin's lymphoma at just 22 but endured was diagnosed with a malignant tumor in 2010, believed to have been caused by the treatment for his earlier cancer.
Rakoff wrote about facing mortality in his book "Half Empty."
"I try to comfort myself with the first-person accounts I've heard of those who die on operating tables and come back: the light, the warmth, and the surge of love from one's dead ancestors urging you forward."
The unmistakable tone of his writing resonated with many. Fans of the award winning writer have taken to Twitter to express their grief.
"Oh no oh no oh no oh no. David Rakoff passed away. My heart is breaking and the literary world is missing a bright light," wrote musician Sarah Bareilles.
"Devastated. David Rakoff was a great, loving, supportive friend -- to me and so many others. Absolutely heartbroken by his death," wrote author Dan Savage.
"Heartbroken to hear about David Rakoff. This piece was one of the most moving pieces of writing I've ever heard: thisamericanlife.org/radio-archives...," tweeted MSNBC host Christopher Hayes who linked to his essay "Speak Now or Forever Hold Your Peace."
A tumblr devoted to Rakoff, which offers a compilation of his greatest quotes, has also been created.
In it, Champion recalls past interviews with the "Half Empty" author notes that he was gracious, always keeping him well fed during their meetings and apologizing for stopping the interview each time he needed to take medication.
"Last night, David lost his battle with cancer," writes Champion. "But we still have the three books, the many 'This American Life' appearances, and David's quiet suggestion that a comic yet realistic dignity is an extraordinary defense against life's cruel setbacks."
According to the official "This American Life" website, Rakoff's final book (a novel written in rhyme) is set to be released in 2013.