Start with The Problems of Philosophy
Published in 1912, about 100 pages, and still the best short introduction to philosophy in English. It begins with a table and asks what you actually know about it, then walks through appearance, matter, idealism, knowledge and induction without a single unnecessary sentence.
If you want something more practical, The Conquest of Happiness (1930) is his advice book, and it's unexpectedly good: unsentimental, unmystical, and blunt about boredom, envy and the fear of public opinion.
| Book | Year | What it is |
|---|---|---|
| The Problems of Philosophy | 1912 | The best short introduction to the subject. Start here. |
| The Conquest of Happiness | 1930 | Practical advice, delivered without mysticism. Better than it sounds. |
| A History of Western Philosophy | 1945 | The bestseller that funded his later life. Opinionated and unreliable in places. |
| Why I Am Not a Christian | 1927 | The lecture, plus related essays. Combative. |
| In Praise of Idleness | 1935 | The title essay argues for a four-hour working day. From 1935. |
| Principia Mathematica | 1910-13 | With Whitehead. Foundational, and essentially unreadable. Admire from a distance. |
About that History
A History of Western Philosophy sold enormously, won him the Nobel, and paid for the rest of his life. It's also the reason many professional philosophers are rude about him.
He's generous to the thinkers he agrees with and dismissive to the point of caricature about the ones he doesn't. Nietzsche gets a chapter that's closer to an assault. Aquinas is barely given a hearing. Continental philosophy after Hegel is largely waved away.
Read it for the prose and the confidence, which are genuinely a pleasure, and check anything you plan to repeat. Anthony Kenny's history is the sober alternative.
The life was not quiet
Imprisoned in 1918 for opposing the First World War, and again in 1961, aged 89, for anti-nuclear protest. Sacked from City College New York in 1940 after a court case about his views on sex and marriage. Married four times. Co-authored the Russell-Einstein Manifesto in 1955.
He also identified the paradox that broke Frege's system, wrote the theory of descriptions that shaped analytic philosophy, and taught Wittgenstein, who then decided Russell had got it wrong.
Around him
The branches of philosophy if you want the map before the reading, and philosophy books for beginners for the wider shelf.
365 Days of Philosophy covers Russell alongside the analytic tradition he founded and the continental one he dismissed.
Common questions
Which Bertrand Russell book should I read first?
The Problems of Philosophy (1912), about 100 pages and still the best short introduction to the subject in English. The Conquest of Happiness is the practical alternative.
Is A History of Western Philosophy reliable?
Not entirely. It's generous to thinkers he liked and caricatures those he didn't, particularly Nietzsche and Aquinas. Read it for the prose and check anything you intend to repeat.
Why did Russell win the Nobel Prize?
In Literature, in 1950, for his writing in defence of humanitarian ideals and freedom of thought. His prose is the clearest in modern philosophy.
Was Russell a good philosopher or just a good writer?
Both. The theory of descriptions and Russell's paradox are foundational technical contributions, quite apart from the popular books.
What is Russell's paradox?
The problem of whether the set of all sets that don't contain themselves contains itself. Either answer contradicts, and it broke Frege's attempt to found mathematics on logic.