Eden Robinson, Rachel Cusk among Giller Prize finalists

On Monday morning, the writer Michael Redhill was leading a walking tour through downtown Toronto, retracing the steps and visiting some of the settings of his 2006 historical novel Consolation, which is partly set in the city in the mid-19th century. Among the 30-odd participants was the author's mother.

"We were standing in Nathan Phillips Square" – the plaza adjacent to Toronto's City Hall – "when the first tweets started coming through," he recalled, a couple of hours later. "We all kind of went wild for 30 seconds, and then we carried on. I turned my phone off because I still had an hour's worth of walking to do… I think my mom might be more excited than I am, so it was really nice to see the look on her face when the news came out."

The celebration-worthy news Redhill had received was that his most recent novel, Bellevue Square, a literary thriller about a woman searching her Toronto neighborhood for her supposed doppelganger, was one of five books shortlisted for this year's Scotiabank Giller Prize.

If this year's shortlist has a theme, it might be second chances: Three of the five authors nominated for the $100,000 prize have been finalists before, yet none of them have won what is arguably Canada's most prestigious literary prize.

Redhill, whose novel was praised as "warm, and funny, and smart" by the jury, was in the same position in 2001, when his debut novel Martin Sloane was shortlisted for the prize. (It lost to Clara Callan by the late Richard B. Wright.)

"When I was nominated in 2001, it was very scary," he said. "I didn't know how to deal with it. The evening itself was surreal – I think I remember four minutes from it. And I desperately didn't want to win; I thought if I won, I would never be forgiven…These many years later, I'm ready for whatever happens."

Another author making a second appearance on the shortlist is Haisla and Heiltsuk author Eden Robinson, whose novel Monkey Beach was a finalist for the Giller in 2000. This time around, the Kitamaat Village, B.C., resident was recognized for Son of a Trickster, which kicks off a planned trilogy about a young man who learns his father is the trickster Wee'git. In their citation, jurors called the novel "energetic, often darkly funny, sometimes poignant" and "a book that will resonate long after the reader has devoured the final page."

Finally, just two years after last appearing on the shortlist with Outline, Saskatchewan-born, U.K.-based writer Rachel Cusk is nominated once again, this time for its sequel, Transit, about a writer who moves into a run-down London apartment with her two young sons. The jury described the novel as "alight with wisdom and humour" and "an exquisitely poised meditation on life, time, and change."

The remaining finalists are Toronto-born, Dublin-based Ed O'Loughlin, author of the historical novel Minds of Winter, which the jury called a "brilliant story of Polar expedition," and New Brunswick writer and artist Michelle Winters for her "original, off-beat" novel I Am A Truck, about a woman whose husband goes missing on the eve of their 20th anniversary, and which the jury said was a "very funny, fully-achieved novel about connection and misunderstanding."

This also marks the first time that Winters's publisher, the Picton, Ont.-based Invisible Publishing, which released its first book in 2007, has placed a book on the Giller shortlist.

"This is a pretty good tenth anniversary present," said Leigh Nash, the publisher, who plucked the manuscript out of the slush pile. "It's an exciting list, and I'm thrilled to be on it. I'm thrilled Michelle's work is on it. I'm thrilled more people are going to read our books – my head is spinning."

Serving on this year's jury are American novelist and short-story writer Nathan Englander; the British author Richard Beard; former Giller Prize winners Lynn Coady and André Alexis, as well as Canadian novelist Anita Rau Badami, who is also jury chair. They considered 112 books for this year's Giller Prize before choosing a longlist of 12 titles, which were announced last month. Of the books longlisted for the prize that were left off the shortlist, the most notable omission was David Chariandy's novel Brother, which was named a finalist for the Rogers Writers' Trust Fiction Prize last week.

"We were looking for originality…we were looking for freshness," said Coady, who won the prize in 2013 for her short-story collection Hellgoing, not long after Monday's announcement. "When you're not nominated you think, 'Ah it's just a crapshoot, it's just a complete matter of whimsy.' But actually being on the jury I realized, no, every book really does get a fair shake. I feel like we really did get in there and weigh the relative merits of every book."

"We are, in the end, just five people who love books," said Beard. "And we've now got five books that we love in particular. And we're just going to have to have a big fight about who loves what most. It should be fun."

The winner of this year's Giller Prize will be announced Nov. 20.

The prize was founded in 1994 by Jack Rabinovitch in honour of his wife, the literary journalist Doris Giller, who had passed away the previous year.

Rabinovitch died in August.