Remove comments from C-like source code

First off, as said in the comments, C-style comments matches the first /* with the first */; meaning you can not nest comments:

/* This comment is /* a nested */ comment */

should be interpreted as: comment */

It is also more natural, in Python, to iterate over the elements of a collection rather than their indices. This allows you to write for character in content:. And if you trully need indices, you can use enumerate.

You can also use temporary variables to store characters that may indicate the beginning or the end of a comment without having to look at the character before or after the current one:

def remove_comments(content):
    block_comment = False
    line_comment = False
    probably_a_comment = False
    result = []
    for character in content:
        if not line_comment and not block_comment and character == '/':
            probably_a_comment = True
            continue

        if block_comment and character == '*':
            probably_a_comment = True
            continue

        if line_comment and character == '\n':
            line_comment = False
            result.append('\n')
        elif block_comment and probably_a_comment and character == '/':
            block_comment = False
        elif not line_comment and not block_comment:
            if probably_a_comment:
                if character == '/':
                    line_comment = True
                elif character == '*':
                    block_comment = True
                else:
                    result.append('/')  # Append the / we skipped when flagging that it was probably a comment starting
                    result.append(character)
            else:
                result.append(character)
        probably_a_comment = False

    return ''.join(result)

You can also simplify a bit the memory management by using a generator instead of appending into a list:

def remove_comments(content):
    def gen_content():
        block_comment = False
        line_comment = False
        probably_a_comment = False
        for character in content:
            if not line_comment and not block_comment and character == '/':
                probably_a_comment = True
                continue

            if block_comment and character == '*':
                probably_a_comment = True
                continue

            if line_comment and character == '\n':
                line_comment = False
                yield '\n'
            elif block_comment and probably_a_comment and character == '/':
                block_comment = False
            elif not line_comment and not block_comment:
                if probably_a_comment:
                    if character == '/':
                        line_comment = True
                    elif character == '*':
                        block_comment = True
                    else:
                        yield '/'
                        yield character
                else:
                    yield character
            probably_a_comment = False

    return ''.join(gen_content())

If you want to go crazy, you can also use a state machine approach to simplify the code: no more boolean flags and far less comparisons in average:

def source_code(char):
    if char == '/':
        return comment_begin, ''
    return source_code, char

def comment_begin(char):
    if char == '/':
        return inline_comment, ''
    if char == '*':
        return block_comment, ''
    return source_code, '/'+char

def inline_comment(char):
    if char == '\n':
         return source_code, char
    return inline_comment, ''

def block_comment(char):
    if char == '*':
        return end_block_comment, ''
    return block_comment, ''

def end_block_comment(char):
    if char == '/':
        return source_code, ''
    return block_comment, ''

def remove_comments(content):
    def gen_content():
        parser = source_code
        for character in content:
            parser, text = parser(character)
            yield text

    return ''.join(gen_content())

But, all in all, this is far too complicated for the task at hand. You can get the same job done using a simple regular expression:

import re


COMMENTS = re.compile(r'''
    (//[^\n]*(?:\n|$))    # Everything between // and the end of the line/file
    |                     # or
    (/\*.*?\*/)           # Everything between /* and */
''', re.VERBOSE)


def remove_comments(content):
    return COMMENTS.sub('\n', content)