Start with the lectures
Introductory Lectures on Psycho-Analysis (1917) is Freud teaching, and he's an excellent teacher: patient, funny, and willing to anticipate the reader's objections before making them himself. It covers slips, dreams and neurosis in sequence.
If you want something shorter, Civilization and Its Discontents (1930) is 100 pages and the one non-specialists still read. Its argument is that civilisation requires renouncing instinct, that the renunciation produces a permanent low-grade unhappiness, and that this is the deal rather than a fixable defect.
| Book | Year | What it does |
|---|---|---|
| Introductory Lectures on Psycho-Analysis | 1917 | The whole system, taught well. Best first. |
| Civilization and Its Discontents | 1930 | Culture as organised renunciation. Short and still argued about. |
| The Interpretation of Dreams | 1900 | The founding text. Long, and the theory is the least durable part. |
| The Psychopathology of Everyday Life | 1901 | Slips, forgetting, small errors. The most entertaining. |
| Beyond the Pleasure Principle | 1920 | The death drive. Written after the First World War, and it shows. |
| The Ego and the Id | 1923 | The structural model. Short and technical. |
What hasn't held up
Being straight about this is more useful than either reverence or dismissal.
Dream interpretation as disguised wish-fulfilment has no empirical support. The Oedipus complex as a universal developmental stage is not accepted. Penis envy and the account of female development were contested in his own lifetime and haven't recovered. The specific case histories look, on re-examination, considerably less conclusive than he presented them, and in places he shaped the evidence to fit.
Psychoanalysis as a treatment has weak outcome evidence compared with CBT for most presenting problems.
What did hold up
That much mental life is not available to introspection is now uncontroversial, though the modern unconscious looks nothing like his. That early relationships shape later ones is well supported. That people defend against knowledge about themselves, through denial, projection and rationalisation, survives in a great deal of current clinical practice.
And the talking cure itself: the idea that describing your experience to an attentive person, over time, changes it. Every therapy since is a variant on that.
Around him
Jung, his heir until the 1913 split. Schopenhauer, whom Freud admitted got to the unconscious first. 365 Days of Psychology runs from Freud through to CBT and the modern research, a page a day, which is the fairest way to see where he sits.
Common questions
Which Freud book should I read first?
Introductory Lectures on Psycho-Analysis (1917), where he's teaching and at his most readable. Civilization and Its Discontents is the shorter alternative at around 100 pages.
Was Freud right about anything?
Yes: that much of mental life is unavailable to introspection, that early relationships shape later ones, that people defend against self-knowledge, and that talking to an attentive person over time changes things.
What did Freud get wrong?
Dream interpretation as disguised wish-fulfilment, the Oedipus complex as universal, his account of female development, and the reliability of his own case histories, several of which he shaped to fit.
Is psychoanalysis still used?
Yes, though far less than a century ago, and CBT has stronger outcome evidence for most common problems. Psychodynamic therapy remains widely practised in modified form.
Is The Interpretation of Dreams worth reading?
As a historical document and a piece of writing, yes. As an account of what dreams are, no. Start elsewhere.