Start with Seize the Day. The obvious alternative is The adventures of Augie March, the 1953 breakthrough that won the National Book Award and announced a new American voice, and it is the wrong first Bellow for a practical reason: it is six hundred pages of exuberant, digressive, self-delighted narration, and that voice is precisely the thing readers either fall for or find insufferable. Seize the Day is barely a hundred pages, it is written in a tighter register, and it delivers the essential Bellow situation — a clever man failing in public, drowning in his own eloquence — in a single afternoon. If it moves you, commit to the big books. If it irritates you, you have lost an hour rather than a fortnight.
Read Herzog second. It is his best novel by the most common critical reckoning, and it is where the method arrives fully formed: a betrayed academic writing unsent letters to the living and the dead, funny and pitiable in the same sentence. It is also more forgiving than its reputation, because the letters break the text into short bursts.
The exuberant novels
Now The adventures of Augie March, which you are ready for. Its famous opening — an American, Chicago-born — is a manifesto, and the book keeps that promise for about four hundred pages and then sprawls. Most readers agree it loses shape in Mexico. Take it as a voice to swim in rather than a plot to follow and it is a marvel.
Henderson, the rain king is the eccentric one and the one Bellow said he loved best: a rich, enormous, unhappy American who goes to an invented Africa to find out what he wants. It is a fable, not a realist novel, and it should be read as such. Some readers find its Africa a problem, and that objection is worth carrying while you read rather than dismissing.
The middle run, which is the reason to be here
Mr. Sammler's Planet and Humboldt's Gift are the difficult, essential pair. Mr. Sammler's Planet is narrated by an elderly Holocaust survivor appalled by 1960s New York, and its politics have made it the most argued-over book in the shelf; the debate about whether the novel endorses Sammler's disgust or exhibits it has run for fifty years and is not settled. Humboldt's Gift is the comedy of the pair — a successful writer haunted by his dead, failed, brilliant friend — and it won the Pulitzer. Read them in that order.
Late Bellow
The dean's December is the weakest of the major novels and the place most readers stop, and there is no shame in stopping there; it is a novel of opinions where the earlier books were novels of appetite. Something to remember me by collects late short fiction, and the compression suits him — several of these novellas are as good as anything he wrote long.
Ravelstein, published when Bellow was eighty-four, is the true late surprise: a short, warm, gossipy portrait of a dying friend, transparently based on Allan Bloom. It caused a stir over how much private life it disclosed. Read it last, when you already know the voice well enough to hear how much it has softened.
Where to stop
The honest recommendation for most readers is five books: Seize the Day, Herzog, The adventures of Augie March, Humboldt's Gift and Ravelstein. That is the arc of the career — early compression, the breakout voice, the mature comedy, the valedictory — without the stretches where Bellow's essayistic tendency overtakes his novelistic one.
James Atlas' Bellow - A Biography is the fullest life, though it is famously cool toward its subject and other biographers have pushed back on its judgements; read it as one account rather than the account. For a very different mid-century American voice, F. Scott Fitzgerald is the useful contrast — the same interest in ambition and self-invention, at a third the word count.
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