"Clever" hides a fork in the road. Some of its synonyms praise honest insight; others accuse you of sly manipulation. Calling someone astute is a compliment; calling them cunning is a warning. Here is the cleverness cluster from 1983, ranked by intensity and split by that nuance.
Shrewd and knowledgeable in practical matters; having know-how.
practical, street-smart
Clever, shrewd, and prudent; careful and steady.
cautious insight
Sharply perceptive; able to assess situations accurately.
honest insight
Quick-thinking and mentally acute.
quick on the uptake
Able to find quick, clever ways to overcome difficulties.
finds a way
Clever at achieving aims by indirect or deceitful methods.
deceptive
Sharp, hard-headed practical judgment; sometimes wily.
works the angles
Cleverly inventive and original in conception.
inventive
Sly skill at deceiving, misleading, or outmaneuvering.
sly
Full of wiles and tricks; craftily strategic.
tricky, fox-like
Skillful, often in a crafty or manipulative way.
skilled manipulation
Coldly strategic and scheming; ruthlessly determined.
cold strategy
Deceitful cunning; the use of tricks or stratagems.
artful deception
Acutely discerning; seeing through pretense.
penetrating insight
Wise; showing keen, farsighted understanding and judgment.
wisdom
Deeply learned and scholarly through study.
book-deep learning
This trio is the whole nuance axis in three words. Astute is honest sharp perception, a clear compliment. Shrewd is harder and more practical, working the angles, still mostly admiring but with an edge. Cunning crosses the line into sly deception. The intelligence is similar; the intent slides from open to hidden.
All three live on the deceptive end. Crafty reaches its aims by indirect, underhanded means. Cunning is sly skill at misleading or outmaneuvering. Wily is full of tricks, the fox who is always a step ahead. Crafty is the method, cunning is the skill, wily is the reputation.
Both are high-end, but they are not the same gift. Sagacious is wisdom: keen, farsighted judgment about people and situations. Erudite is learning: deep knowledge gained from study. You can be sagacious without a single degree, and erudite without an ounce of practical sense.
Both mean sharp judgment. Astute leans toward perception and discernment and is broadly positive. Shrewd is harder-headed and practical, often about money or advantage, and it can shade toward wiliness. Astute notices; shrewd works the angles.
Usually not. Cunning emphasizes cleverness at deceiving or outmaneuvering, so it carries a wary or negative connotation, unlike astute, ingenious, or sagacious, which praise the intelligence itself.
Crafty, cunning, wily, artful, and calculating all describe cleverness aimed at deceiving or manipulating. Guile is the noun for that quality.
Sagacious is the best fit: wise with farsighted judgment. Perspicacious (seeing through pretense) and astute (sharply perceptive) are close, and erudite means clever through deep learning.
1983 maps the cleverness cluster, and hundreds of others, as a field you can tap through, with recorded audio for every word and quizzes that test whether you can place a word among its neighbors.