It’s Eisner Awards season – that time of year when the comic book industry’s best and brightest are recognised for their creative achievements over the past year. Voting is currently underway ahead of the virtual awards ceremony next month, so while we wait for winners to be announced, let’s take a look back at the work of the cartoonist who gave the awards their name: Will Eisner.

Responsible for popularising the “graphic novel” label and approach, Eisner was an early advocate for treating comics as a serious art form – an argument he backed up with his consummate skill as both a writer and artist. Indeed, from The Spirit strip in the 1940s to 1978’s A Contract with God, and Other Tenement Stories and right on through to his death in 2005, Eisner continued to push the boundaries of what the medium was capable of.

Eisner’s work spawned countless imitators, including fellow comics legends Neil Gaiman, Alan Moore, and Frank Miller, and he taught entire generations the comics craft through seminal non-fiction tomes Comics and Sequential Art and Graphic Storytelling and Visual Narrative.

Which Eisner stories rate as the cartoonist’s very best? It’s a tough call, but this is awards season after all – so, with this in mind, here are my top five picks for the greatest Will Eisner comics of all time.

1. Life on Another Planet

A rare foray into science fiction by Eisner, Life on Another Planet is nevertheless grounded by the same humanistic approach that characterises the cartoonist’s other, less sensationalist works. Indeed, this 1983 graphic novel – which explores the fallout of humanity making first contact with an unseen alien race during the Cold War – functions as more of a slow burn thriller/social satire than anything else.

It’s also an unflinchingly pessimistic read. While Eisner rarely shied away from depicting humankind’s less flattering traits, Life on Another Planet sees him really dial up the cynicism, with our collective pettiness, tribalism, and self interest driving the plot more than the book’s understated sci-fi elements. The result is a graphic novel that’s not always an easy read – but one well worth your time, all the same.

2. Fagin the Jew

Eisner’s Jewish heritage was a recurring theme through his career, so it’s fitting that for his penultimate work of fiction, Fagin the Jew, he decided to tackle one of literature’s most prominent examples of anti-Semitism. Released in 2003, Fagin the Jew is a retelling of Charles Dickens’ Oliver Twist from (as its title suggests) Fagin’s perspective, and portrays its titular character in a decidedly more sympathetic light.

Extrapolating on Dickens’ own threadbare characterisation, Eisner recounts Fagin’s experiences as a poorly treated Ashkenazi Jew in 19th Century London to offer a more nuanced portrait than one-dimensional, irredeemably wicked miser. It proves to be a master stroke; by recasting Fagin as a ordinary man driven to crime by providence and prejudice, Eisner poignantly illustrates how bad luck and bigotry can make a villain out of anyone.

3. The Spirit

Don’t be put off by the forgettable 2008 big screen adaptation of The Spirit: this pulpy superhero series is one of the most innovative and influential comics of all time. The Spirit represents Eisner starting to really cut loose, and the fruits of that experimentation – inventive page layouts, genre-bending stories that blend noir, comedy, horror and romance elements, and relatable, flawed characters – are dazzling to behold.

Admittedly, some of the content hasn’t aged well (like the Spirit’s Black sidekick Ebony White, with his blackface-inspired look and Minstrel Show dialect) and may offend modern readers. But if you can overlook this distasteful material, you’ll find that, in terms of raw creative power, The Spirit is hard to top.

4. The Dreamer

The Dreamer is a must-read for anyone interested in the behind-the-scenes story of comics’ Golden Age. Essentially an autobiographical work, this 1986 graphic novel charts Eisner’s career at Eisner & Iger Studios during the 1930s, with thinly veiled stand-ins (barely) obscuring the real people and events involved… and if even half of it is true, boy, were those wild times for the industry.

Eisner recounts everything from court hearings to run-ins with underworld heavies – heck, even bootleg porno comics get thrown into the mix! What’s likely to appeal to comics history aficionados most, however, is Eisner’s depiction of several of the biggest names from the era, including Batman co-creator Bob Kane and Marvel Comics co-architect Jack Kirby. Other books may offer a more complete, accurate account of the Golden Age than The Dreamer, but few (if any) can match the book’s first-hand vitality.

5. A Contract with God

Eisner’s most celebrated fictional work, A Contract with God and Other Tenement Stories was instrumental in shifting mainstream attitudes towards comics’ artistic merit. Funnily enough, though, A Contract with God’s “graphic novel” label is a bit of a misnomer, since it’s really a collection of four short stories set in the same tenement building and united by shared themes including violence, sexual assault, poverty, unfilled desire, and the Jewish immigrant experience.

This last aspect – capturing a snapshot of Jewish-American life in the early 20th Century – is arguably just as important as A Contract with God’s formalist breakthroughs. Drawing upon his own history, Eisner opens a vivid, unvarnished window into what it meant to be a Jew in New York during the Great Depression, drawing praise from academics for his contribution to wider ethnic American literature. So, novel or not, A Contract with God remains a towering achievement that demands to be read by comics fans and non-fans alike.

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What’s your favourite Will Eisner story? Let me know in the comments below, or on Twitter or Facebook!