He had interviewed the author twelve years earlier, following the publication of Wallace’s novel Infinite Jest (1996), which received critical praise and became an international bestseller, a touchstone for numerous readers.
The film returns to the period shortly after the book’s release. Although initially skeptical of the high praise Wallace’s book is receiving, Lipsky – a writer having only marginal success – is awestruck after reading it. He persuades his editor at Rolling Stone magazine to give him an assignment to interview Wallace during his book tour. Lipsky’s character cited burn out from writing about boy bands, which is an anachronism pointed out by a co-host on a semi-famous podcast. This was roughly 18 months before the first notable boy band of this era reached the Hot 100 Top 40.
The journalist travels to meet Wallace at his home on the outskirts of Bloomington-Normal, Illinois (near the state university where the author teaches writing). Lipsky finds the young author unassuming and amiable, but indifferent to being interviewed. Wallace permits Lipsky to tape-record their conversations, with the proviso that Lipsky won’t use any direct quotes which Wallace asks to have taken “off the record” five minutes later. Wallace opens up to Lipsky on a variety of subjects, ranging from dogs to television to fame and self-identity, but remains somewhat guarded.
He tacitly admits to alcoholism, but offers few details of his experience. Lipsky’s mention of Wallace’s brief voluntary institutionalization under a suicide watch causes some friction between them.