diff --git a/docs/api.md b/docs/api.md
index cd186926..fd0cab2f 100644
--- a/docs/api.md
+++ b/docs/api.md
@@ -125,23 +125,34 @@ Scale output to `width` x `height`. By default, the resized image is cropped to
 
 `height` is the integral Number of pixels high the resultant image should be, between 1 and 16383. Use `null` or `undefined` to auto-scale the height to match the width.
 
-#### crop([gravity])
+#### crop([option])
 
 Crop the resized image to the exact size specified, the default behaviour.
 
-`gravity`, if present, is a String or an attribute of the `sharp.gravity` Object e.g. `sharp.gravity.north`.
+`option`, if present, is an attribute of:
 
-Possible values are `north`, `northeast`, `east`, `southeast`, `south`, `southwest`, `west`, `northwest`, `center` and `centre`.
-The default gravity is `center`/`centre`.
+* `sharp.gravity` e.g. `sharp.gravity.north`, to crop to an edge or corner, or
+* `sharp.strategy` e.g. `sharp.strategy.entropy`, to crop dynamically.
+
+Possible attributes of `sharp.gravity` are
+`north`, `northeast`, `east`, `southeast`, `south`,
+`southwest`, `west`, `northwest`, `center` and `centre`.
+
+`sharp.strategy` currently contains only the experimental `entropy`,
+which will retain the part of the image with the highest
+[Shannon entropy](https://en.wikipedia.org/wiki/Entropy_%28information_theory%29) value.
+
+The default option is a `center`/`centre` gravity.
 
 ```javascript
 var transformer = sharp()
-  .resize(300, 200)
-  .crop(sharp.gravity.north)
+  .resize(200, 200)
+  .crop(sharp.strategy.entropy)
   .on('error', function(err) {
     console.log(err);
   });
-// Read image data from readableStream, resize and write image data to writableStream
+// Read image data from readableStream
+// Write 200px square auto-cropped image data to writableStream
 readableStream.pipe(transformer).pipe(writableStream);
 ```
 
diff --git a/docs/changelog.md b/docs/changelog.md
index 4bac9062..866114d4 100644
--- a/docs/changelog.md
+++ b/docs/changelog.md
@@ -14,6 +14,10 @@
   [#239](https://github.com/lovell/sharp/issues/239)
   [@chrisriley](https://github.com/chrisriley)
 
+* Add entropy-based strategy to determine crop region.
+  [#295](https://github.com/lovell/sharp/issues/295)
+  [@rightaway](https://github.com/rightaway)
+
 * Expose density metadata; set density of images from vector input.
   [#338](https://github.com/lovell/sharp/issues/338)
   [@lookfirst](https://github.com/lookfirst)
diff --git a/index.js b/index.js
index 65ad0c09..dbb70a48 100644
--- a/index.js
+++ b/index.js
@@ -64,7 +64,7 @@ var Sharp = function(input, options) {
     width: -1,
     height: -1,
     canvas: 'crop',
-    gravity: 0,
+    crop: 0,
     angle: 0,
     rotateBeforePreExtract: false,
     flip: false,
@@ -231,48 +231,53 @@ Sharp.prototype._write = function(chunk, encoding, callback) {
   }
 };
 
-// Crop this part of the resized image (Center/Centre, North, East, South, West)
+// Weighting to apply to image crop
 module.exports.gravity = {
-  'center': 0,
-  'centre': 0,
-  'north': 1,
-  'east': 2,
-  'south': 3,
-  'west': 4,
-  'northeast': 5,
-  'southeast': 6,
-  'southwest': 7,
-  'northwest': 8
+  center: 0,
+  centre: 0,
+  north: 1,
+  east: 2,
+  south: 3,
+  west: 4,
+  northeast: 5,
+  southeast: 6,
+  southwest: 7,
+  northwest: 8
 };
 
-Sharp.prototype.crop = function(gravity) {
+// Strategies for automagic behaviour
+module.exports.strategy = {
+  entropy: 16
+};
+
+/*
+  What part of the image should be retained when cropping?
+*/
+Sharp.prototype.crop = function(crop) {
   this.options.canvas = 'crop';
-  if (!isDefined(gravity)) {
-    this.options.gravity = module.exports.gravity.center;
-  } else if (isInteger(gravity) && inRange(gravity, 0, 8)) {
-    this.options.gravity = gravity;
-  } else if (isString(gravity) && isInteger(module.exports.gravity[gravity])) {
-    this.options.gravity = module.exports.gravity[gravity];
+  if (!isDefined(crop)) {
+    // Default
+    this.options.crop = module.exports.gravity.center;
+  } else if (isInteger(crop) && inRange(crop, 0, 8)) {
+    // Gravity (numeric)
+    this.options.crop = crop;
+  } else if (isString(crop) && isInteger(module.exports.gravity[crop])) {
+    // Gravity (string)
+    this.options.crop = module.exports.gravity[crop];
+  } else if (isInteger(crop) && crop === module.exports.strategy.entropy) {
+    // Strategy
+    this.options.crop = crop;
   } else {
-    throw new Error('Unsupported crop gravity ' + gravity);
+    throw new Error('Unsupported crop ' + crop);
   }
   return this;
 };
 
 Sharp.prototype.extract = function(options) {
-  if (!options || typeof options !== 'object') {
-    // Legacy extract(top,left,width,height) syntax
-    options = {
-      left: arguments[1],
-      top: arguments[0],
-      width: arguments[2],
-      height: arguments[3]
-    };
-  }
   var suffix = this.options.width === -1 && this.options.height === -1 ? 'Pre' : 'Post';
   ['left', 'top', 'width', 'height'].forEach(function (name) {
     var value = options[name];
-    if (typeof value === 'number' && !Number.isNaN(value) && value % 1 === 0 && value >= 0) {
+    if (isInteger(value) && value >= 0) {
       this.options[name + (name === 'left' || name === 'top' ? 'Offset' : '') + suffix] = value;
     } else {
       throw new Error('Non-integer value for ' + name + ' of ' + value);
diff --git a/src/operations.cc b/src/operations.cc
index be3c97a9..ad9f8406 100644
--- a/src/operations.cc
+++ b/src/operations.cc
@@ -170,4 +170,82 @@ namespace sharp {
     }
   }
 
+  /*
+    Calculate crop area based on image entropy
+  */
+  std::tuple<int, int> EntropyCrop(VImage image, int const outWidth, int const outHeight) {
+    int left = 0;
+    int top = 0;
+    int const inWidth = image.width();
+    int const inHeight = image.height();
+    if (inWidth > outWidth) {
+      // Reduce width by repeated removing slices from edge with lowest entropy
+      int width = inWidth;
+      double leftEntropy = 0.0;
+      double rightEntropy = 0.0;
+      // Max width of each slice
+      int const maxSliceWidth = static_cast<int>(ceil((inWidth - outWidth) / 8.0));
+      while (width > outWidth) {
+        // Width of current slice
+        int const slice = std::min(width - outWidth, maxSliceWidth);
+        if (leftEntropy == 0.0) {
+          // Update entropy of left slice
+          leftEntropy = Entropy(image.extract_area(left, 0, slice, inHeight));
+        }
+        if (rightEntropy == 0.0) {
+          // Update entropy of right slice
+          rightEntropy = Entropy(image.extract_area(width - slice - 1, 0, slice, inHeight));
+        }
+        // Keep slice with highest entropy
+        if (leftEntropy >= rightEntropy) {
+          // Discard right slice
+          rightEntropy = 0.0;
+        } else {
+          // Discard left slice
+          leftEntropy = 0.0;
+          left = left + slice;
+        }
+        width = width - slice;
+      }
+    }
+    if (inHeight > outHeight) {
+      // Reduce height by repeated removing slices from edge with lowest entropy
+      int height = inHeight;
+      double topEntropy = 0.0;
+      double bottomEntropy = 0.0;
+      // Max height of each slice
+      int const maxSliceHeight = static_cast<int>(ceil((inHeight - outHeight) / 8.0));
+      while (height > outHeight) {
+        // Height of current slice
+        int const slice = std::min(height - outHeight, maxSliceHeight);
+        if (topEntropy == 0.0) {
+          // Update entropy of top slice
+          topEntropy = Entropy(image.extract_area(0, top, inWidth, slice));
+        }
+        if (bottomEntropy == 0.0) {
+          // Update entropy of bottom slice
+          bottomEntropy = Entropy(image.extract_area(0, height - slice - 1, inWidth, slice));
+        }
+        // Keep slice with highest entropy
+        if (topEntropy >= bottomEntropy) {
+          // Discard bottom slice
+          bottomEntropy = 0.0;
+        } else {
+          // Discard top slice
+          topEntropy = 0.0;
+          top = top + slice;
+        }
+        height = height - slice;
+      }
+    }
+    return std::make_tuple(left, top);
+  }
+
+  /*
+    Calculate the Shannon entropy for an image
+  */
+  double Entropy(VImage image) {
+    return image.hist_find().hist_entropy();
+  }
+
 }  // namespace sharp
diff --git a/src/operations.h b/src/operations.h
index 059d8188..5ece5743 100644
--- a/src/operations.h
+++ b/src/operations.h
@@ -33,6 +33,16 @@ namespace sharp {
    */
   VImage Sharpen(VImage image, int const radius, double const flat, double const jagged);
 
+  /*
+    Calculate crop area based on image entropy
+  */
+  std::tuple<int, int> EntropyCrop(VImage image, int const outWidth, int const outHeight);
+
+  /*
+    Calculate the Shannon entropy for an image
+  */
+  double Entropy(VImage image);
+
 }  // namespace sharp
 
 #endif  // SRC_OPERATIONS_H_
diff --git a/src/pipeline.cc b/src/pipeline.cc
index a4f3e91d..41a992c0 100644
--- a/src/pipeline.cc
+++ b/src/pipeline.cc
@@ -49,6 +49,7 @@ using sharp::Normalize;
 using sharp::Gamma;
 using sharp::Blur;
 using sharp::Sharpen;
+using sharp::EntropyCrop;
 
 using sharp::ImageType;
 using sharp::ImageTypeId;
@@ -506,9 +507,15 @@ class PipelineWorker : public AsyncWorker {
           // Crop/max/min
           int left;
           int top;
-          std::tie(left, top) = CalculateCrop(
-            image.width(), image.height(), baton->width, baton->height, baton->gravity
-          );
+          if (baton->crop < 9) {
+            // Gravity-based crop
+            std::tie(left, top) = CalculateCrop(
+              image.width(), image.height(), baton->width, baton->height, baton->crop
+            );
+          } else {
+            // Entropy-based crop
+            std::tie(left, top) = EntropyCrop(image, baton->width, baton->height);
+          }
           int width = std::min(image.width(), baton->width);
           int height = std::min(image.height(), baton->height);
           image = image.extract_area(left, top, width, height);
@@ -996,7 +1003,7 @@ NAN_METHOD(pipeline) {
   baton->overlayGravity = attrAs<int32_t>(options, "overlayGravity");
   // Resize options
   baton->withoutEnlargement = attrAs<bool>(options, "withoutEnlargement");
-  baton->gravity = attrAs<int32_t>(options, "gravity");
+  baton->crop = attrAs<int32_t>(options, "crop");
   baton->interpolator = attrAsStr(options, "interpolator");
   // Operators
   baton->flatten = attrAs<bool>(options, "flatten");
diff --git a/src/pipeline.h b/src/pipeline.h
index 4f473bfe..eba987e3 100644
--- a/src/pipeline.h
+++ b/src/pipeline.h
@@ -45,7 +45,7 @@ struct PipelineBaton {
   int height;
   int channels;
   Canvas canvas;
-  int gravity;
+  int crop;
   std::string interpolator;
   double background[4];
   bool flatten;
@@ -99,7 +99,7 @@ struct PipelineBaton {
     topOffsetPost(-1),
     channels(0),
     canvas(Canvas::CROP),
-    gravity(0),
+    crop(0),
     flatten(false),
     negate(false),
     blurSigma(0.0),
diff --git a/test/fixtures/expected/crop-entropy.jpg b/test/fixtures/expected/crop-entropy.jpg
new file mode 100644
index 00000000..c1c08061
Binary files /dev/null and b/test/fixtures/expected/crop-entropy.jpg differ
diff --git a/test/fixtures/expected/crop-entropy.png b/test/fixtures/expected/crop-entropy.png
new file mode 100644
index 00000000..1c8a3780
Binary files /dev/null and b/test/fixtures/expected/crop-entropy.png differ
diff --git a/test/unit/crop.js b/test/unit/crop.js
index a3228166..5463ea37 100644
--- a/test/unit/crop.js
+++ b/test/unit/crop.js
@@ -5,9 +5,9 @@ var assert = require('assert');
 var sharp = require('../../index');
 var fixtures = require('../fixtures');
 
-describe('Crop gravities', function() {
+describe('Crop', function() {
 
-  var testSettings = [
+  [
     {
       name: 'North',
       width: 320,
@@ -50,6 +50,13 @@ describe('Crop gravities', function() {
       gravity: sharp.gravity.centre,
       fixture: 'gravity-centre.jpg'
     },
+    {
+      name: 'Default (centre)',
+      width: 80,
+      height: 320,
+      gravity: undefined,
+      fixture: 'gravity-centre.jpg'
+    },
     {
       name: 'Northeast',
       width: 320,
@@ -106,10 +113,8 @@ describe('Crop gravities', function() {
       gravity: sharp.gravity.northwest,
       fixture: 'gravity-west.jpg'
     }
-  ];
-
-  testSettings.forEach(function(settings) {
-    it(settings.name, function(done) {
+  ].forEach(function(settings) {
+    it(settings.name + ' gravity', function(done) {
       sharp(fixtures.inputJpg)
         .resize(settings.width, settings.height)
         .crop(settings.gravity)
@@ -122,7 +127,7 @@ describe('Crop gravities', function() {
     });
   });
 
-  it('allows specifying the gravity as a string', function(done) {
+  it('Allows specifying the gravity as a string', function(done) {
     sharp(fixtures.inputJpg)
       .resize(80, 320)
       .crop('east')
@@ -134,36 +139,57 @@ describe('Crop gravities', function() {
       });
   });
 
-  it('Invalid number', function() {
+  it('Invalid values fail', function() {
     assert.throws(function() {
-      sharp(fixtures.inputJpg).crop(9);
+      sharp().crop(9);
+    });
+    assert.throws(function() {
+      sharp().crop(1.1);
+    });
+    assert.throws(function() {
+      sharp().crop(-1);
+    });
+    assert.throws(function() {
+      sharp().crop('zoinks');
     });
   });
 
-  it('Invalid string', function() {
-    assert.throws(function() {
-      sharp(fixtures.inputJpg).crop('yadda');
-    });
-  });
-
-  it('does not throw if crop gravity is undefined', function() {
+  it('Uses default value when none specified', function() {
     assert.doesNotThrow(function() {
-      sharp(fixtures.inputJpg).crop();
+      sharp().crop();
     });
   });
 
-  it('defaults crop gravity to sharp.gravity.center', function(done) {
-    var centerGravitySettings = testSettings.filter(function (settings) {
-      return settings.name === 'Center';
-    })[0];
-    sharp(fixtures.inputJpg)
-      .resize(centerGravitySettings.width, centerGravitySettings.height)
-      .crop()
-      .toBuffer(function(err, data, info) {
-        if (err) throw err;
-        assert.strictEqual(centerGravitySettings.width, info.width);
-        assert.strictEqual(centerGravitySettings.height, info.height);
-        fixtures.assertSimilar(fixtures.expected(centerGravitySettings.fixture), data, done);
-      });
+  describe('Entropy-based strategy', function() {
+
+    it('JPEG', function(done) {
+      sharp(fixtures.inputJpgWithCmykProfile)
+        .resize(80, 320)
+        .crop(sharp.strategy.entropy)
+        .toBuffer(function(err, data, info) {
+          if (err) throw err;
+          assert.strictEqual('jpeg', info.format);
+          assert.strictEqual(3, info.channels);
+          assert.strictEqual(80, info.width);
+          assert.strictEqual(320, info.height);
+          fixtures.assertSimilar(fixtures.expected('crop-entropy.jpg'), data, done);
+        });
+    });
+
+    it('PNG', function(done) {
+      sharp(fixtures.inputPngWithTransparency)
+        .resize(320, 80)
+        .crop(sharp.strategy.entropy)
+        .toBuffer(function(err, data, info) {
+          if (err) throw err;
+          assert.strictEqual('png', info.format);
+          assert.strictEqual(4, info.channels);
+          assert.strictEqual(320, info.width);
+          assert.strictEqual(80, info.height);
+          fixtures.assertSimilar(fixtures.expected('crop-entropy.png'), data, done);
+        });
+    });
+
   });
+
 });
diff --git a/test/unit/extract.js b/test/unit/extract.js
index 2191c618..f49c8e92 100644
--- a/test/unit/extract.js
+++ b/test/unit/extract.js
@@ -6,29 +6,6 @@ var sharp = require('../../index');
 var fixtures = require('../fixtures');
 
 describe('Partial image extraction', function() {
-  describe('using the legacy extract(top,left,width,height) syntax', function () {
-    it('JPEG', function(done) {
-      sharp(fixtures.inputJpg)
-        .extract(2, 2, 20, 20)
-        .toBuffer(function(err, data, info) {
-          if (err) throw err;
-          assert.strictEqual(20, info.width);
-          assert.strictEqual(20, info.height);
-          fixtures.assertSimilar(fixtures.expected('extract.jpg'), data, done);
-        });
-    });
-
-    it('PNG', function(done) {
-      sharp(fixtures.inputPng)
-        .extract(300, 200, 400, 200)
-        .toBuffer(function(err, data, info) {
-          if (err) throw err;
-          assert.strictEqual(400, info.width);
-          assert.strictEqual(200, info.height);
-          fixtures.assertSimilar(fixtures.expected('extract.png'), data, done);
-      });
-    });
-  });
 
   it('JPEG', function(done) {
     sharp(fixtures.inputJpg)