diff --git a/escodegen.js b/escodegen.js
index 847fc370..eb06961f 100644
--- a/escodegen.js
+++ b/escodegen.js
@@ -229,6 +229,60 @@
         return len && esutils.code.isLineTerminator(str.charCodeAt(len - 1));
     }
 
+    function removeComments(str) {
+        // https://stackoverflow.com/a/59094308
+        return str.replace(/\/\*[\s\S]*?\*\/|\/\/.*/g, '');
+    }
+
+    function removeTrailingWhiteSpaces(str) {
+        return str.replace(/\S(\s+)$/g, '');
+    }
+
+    function isParenthesized(str, leftPar, rightPar) {
+        str = removeComments(str);
+        str = removeTrailingWhiteSpaces(str);
+        var counter = 0;
+        for (var i = 0; i < str.length; ++i) {
+            if (str[i] == leftPar) {
+                counter++;
+            }
+            else if (str[i] == rightPar) {
+                if (counter == 0) {
+                    return false;
+                }
+                counter--;
+            }
+        }
+        return counter == 0 && str[str.length-1] == rightPar;
+    }
+
+    function isParenthesizedByAnyBracketKind(str) {
+        return isParenthesized(str, '(', ')') ||
+                isParenthesized(str, '{', '}') ||
+                isParenthesized(str, '[', ']');
+    }
+
+    function shouldParenthesize(str, parent) {
+        if (!hasLineTerminator(str)) {
+            return false;
+        }
+        if (parent !== undefined && (
+            parent.type == Syntax.ObjectExpression ||
+            parent.type == Syntax.ArrayExpression ||
+            parent.type == Syntax.Property
+            )) {
+            return false;
+        }
+        if (!isParenthesizedByAnyBracketKind(str)) {
+            return true;
+        }
+
+        str = removeComments(str);
+        var firstNewlineIdx = str.indexOf(newline);
+        var firstParenthesisIdx = str.match(/[\(\[\{)]/).index;
+        return firstNewlineIdx < firstParenthesisIdx;
+    }
+
     function merge(target, override) {
         var key;
         for (key in override) {
@@ -570,6 +624,18 @@
         return [base, stmt];
     }
 
+    function addMultiLineIndent(stmt) {
+        var str = base + flattenToString(stmt);
+        var split = str.split(/\n/g);
+        var suffix = '';
+        // do not replace the last newline
+        if (split[split.length-1].length == 0) {
+            split = split.slice(0, split.length-1);
+            suffix = newline;
+        }
+        return split.join(newline + base) + suffix;
+    }
+
     function withIndent(fn) {
         var previousBase;
         previousBase = base;
@@ -659,7 +725,7 @@
         return '/*' + comment.value + '*/';
     }
 
-    function addComments(stmt, result) {
+    function addComments(stmt, result, parent) {
         var i, len, comment, save, tailingToStatement, specialBase, fragment,
             extRange, range, prevRange, prefix, infix, suffix, count;
 
@@ -703,10 +769,12 @@
             } else {
                 comment = stmt.leadingComments[0];
                 result = [];
+
                 if (safeConcatenation && stmt.type === Syntax.Program && stmt.body.length === 0) {
                     result.push('\n');
                 }
                 result.push(generateComment(comment));
+
                 if (!endsWithLineTerminator(toSourceNodeWhenNeeded(result).toString())) {
                     result.push('\n');
                 }
@@ -721,7 +789,26 @@
                 }
             }
 
-            result.push(addIndent(save));
+            if (!isExpression(stmt)) {
+                result.push(addIndent(save));
+            } else {
+                var text = toSourceNodeWhenNeeded(result).toString();
+                if (shouldParenthesize(text, parent)) {
+                    withIndent(function () {
+                        result = addMultiLineIndent(result);
+                    });
+
+                    result = ['(', newline, result];
+
+                    withIndent(function () {
+                        result.push(addMultiLineIndent(save));
+                    });
+
+                    result.push([newline, base, ')']);
+                } else {
+                    result.push(addIndent(save));
+                }
+            }
         }
 
         if (stmt.trailingComments) {
@@ -977,14 +1064,14 @@
         return result;
     };
 
-    CodeGenerator.prototype.generatePropertyKey = function (expr, computed) {
+    CodeGenerator.prototype.generatePropertyKey = function (expr, computed, parent) {
         var result = [];
 
         if (computed) {
             result.push('[');
         }
 
-        result.push(this.generateExpression(expr, Precedence.Assignment, E_TTT));
+        result.push(this.generateExpression(expr, Precedence.Assignment, E_TTT, parent));
 
         if (computed) {
             result.push(']');
@@ -2095,7 +2182,7 @@
                         }
                     } else {
                         result.push(multiline ? indent : '');
-                        result.push(that.generateExpression(expr.elements[i], Precedence.Assignment, E_TTT));
+                        result.push(that.generateExpression(expr.elements[i], Precedence.Assignment, E_TTT, expr));
                     }
                     if (i + 1 < iz) {
                         result.push(',' + (multiline ? newline : space));
@@ -2155,7 +2242,7 @@
             if (expr.kind === 'get' || expr.kind === 'set') {
                 return [
                     expr.kind, noEmptySpace(),
-                    this.generatePropertyKey(expr.key, expr.computed),
+                    this.generatePropertyKey(expr.key, expr.computed, expr),
                     this.generateFunctionBody(expr.value)
                 ];
             }
@@ -2164,19 +2251,19 @@
                 if (expr.value.type === "AssignmentPattern") {
                     return this.AssignmentPattern(expr.value, Precedence.Sequence, E_TTT);
                 }
-                return this.generatePropertyKey(expr.key, expr.computed);
+                return this.generatePropertyKey(expr.key, expr.computed, expr);
             }
 
             if (expr.method) {
                 return [
                     generateMethodPrefix(expr),
-                    this.generatePropertyKey(expr.key, expr.computed),
+                    this.generatePropertyKey(expr.key, expr.computed, expr),
                     this.generateFunctionBody(expr.value)
                 ];
             }
 
             return [
-                this.generatePropertyKey(expr.key, expr.computed),
+                this.generatePropertyKey(expr.key, expr.computed, expr),
                 ':' + space,
                 this.generateExpression(expr.value, Precedence.Assignment, E_TTT)
             ];
@@ -2191,7 +2278,7 @@
             multiline = expr.properties.length > 1;
 
             withIndent(function () {
-                fragment = that.generateExpression(expr.properties[0], Precedence.Sequence, E_TTT);
+                fragment = that.generateExpression(expr.properties[0], Precedence.Sequence, E_TTT, expr);
             });
 
             if (!multiline) {
@@ -2216,7 +2303,7 @@
                     result.push(',' + newline);
                     for (i = 1, iz = expr.properties.length; i < iz; ++i) {
                         result.push(indent);
-                        result.push(that.generateExpression(expr.properties[i], Precedence.Sequence, E_TTT));
+                        result.push(that.generateExpression(expr.properties[i], Precedence.Sequence, E_TTT, expr));
                         if (i + 1 < iz) {
                             result.push(',' + newline);
                         }
@@ -2484,7 +2571,7 @@
 
     merge(CodeGenerator.prototype, CodeGenerator.Expression);
 
-    CodeGenerator.prototype.generateExpression = function (expr, precedence, flags) {
+    CodeGenerator.prototype.generateExpression = function (expr, precedence, flags, parent) {
         var result, type;
 
         type = expr.type || Syntax.Property;
@@ -2497,8 +2584,9 @@
 
 
         if (extra.comment) {
-            result = addComments(expr, result);
+            result = addComments(expr, result, parent);
         }
+
         return toSourceNodeWhenNeeded(result, expr);
     };
 
diff --git a/test/comment/comment-as-first-element-in-parenthesis-expression.expected.js b/test/comment/comment-as-first-element-in-parenthesis-expression.expected.js
new file mode 100644
index 00000000..f1a36326
--- /dev/null
+++ b/test/comment/comment-as-first-element-in-parenthesis-expression.expected.js
@@ -0,0 +1,73 @@
+let variable = (
+    // comment
+    3 + 3
+);
+let variable = (
+    // comment
+    3 + 3
+);
+let variable = (
+    /* comment */
+    3 + 3
+);
+let variable = (
+    /* comment
+    comment
+    comment
+    */
+    3 + 3
+);
+let variable = (
+    // comment
+    /* comment */
+    // comment
+    3 + 3
+);
+let variable = (
+    // comment
+    3 + 3
+);
+let variable = (
+    // one
+    3 + 3
+) - (
+    // two
+    (1 + 1)
+);
+function foo(a, b, c) {
+    return (
+        // comment
+        a >= b && a <= c || a === 42 || a === 666
+    );
+}
+function foo(a, b, c) {
+    return (
+        // comment
+        a >= b && a <= c
+    ) || a === 42 || a === 666;
+}
+function foo(a, b, c) {
+    throw (
+        // comment
+        a >= b && a <= c || a === 42 || a === 666
+    );
+}
+let arrowFn = () => (
+    // comment
+    {
+        a: 1,
+        b: 2
+    }
+);
+var test = [
+    /**
+     * Test 2
+     */
+    a,
+    /*
+     * Test 1
+     */
+    2,
+    // Test 3
+    3 + 3
+];
diff --git a/test/comment/comment-as-first-element-in-parenthesis-expression.js b/test/comment/comment-as-first-element-in-parenthesis-expression.js
new file mode 100644
index 00000000..e87d0528
--- /dev/null
+++ b/test/comment/comment-as-first-element-in-parenthesis-expression.js
@@ -0,0 +1,87 @@
+let variable = (
+    // comment
+    3+3
+);
+
+let variable = ( // comment
+    3+3
+);
+
+let variable = ( /* comment */
+    3+3
+);
+
+let variable = ( /* comment
+    comment
+    comment
+    */
+    3+3
+);
+
+let variable = (
+    // comment
+    /* comment */
+    // comment
+    3+3
+);
+
+let variable = /* comment */ (
+    // comment
+    3+3
+);
+
+let variable = (
+    (
+        // one
+        3+3
+    ) -
+    (
+        // two
+        1+1
+    )
+);
+
+function foo(a, b, c) {
+    return (
+        // comment
+        (a >= b && a <= c)
+        || a === 42 || a === 666
+    );
+}
+
+function foo(a, b, c) {
+    return (
+        ( // comment
+            a >= b &&
+            a <= c)
+        || a === 42 || a === 666
+    );
+}
+
+function foo(a, b, c) {
+    throw (
+        // comment
+        (a >= b && a <= c)
+        || a === 42 || a === 666
+    );
+}
+
+let arrowFn = () => (
+    // comment
+    {
+      a: 1, b: 2
+    }
+);
+
+var test = [
+    /**
+     * Test 2
+     */
+    a,
+    /*
+     * Test 1
+     */
+    2,
+    // Test 3
+    3+3
+];