```python
"""Prune a file listing with ordered drop and keep rules."""


def prune_listing(listing: list, rules: list) -> list:
    def segment_fits(pattern: str, text: str) -> bool:
        p = t = mark = 0
        star = -1
        while t < len(text):
            if p < len(pattern) and pattern[p] == "*":
                star = p
                mark = t
                p += 1
            elif p < len(pattern) and pattern[p] == text[t]:
                p += 1
                t += 1
            elif star >= 0:
                p = star + 1
                mark += 1
                t = mark
            else:
                return False
        while p < len(pattern) and pattern[p] == "*":
            p += 1
        return p == len(pattern)

    def split_strict(text: str, what: str) -> list:
        if not isinstance(text, str) or text == "":
            raise ValueError(f"{what} must be a non-empty string")
        segments = text.split("/")
        if any(segment == "" for segment in segments):
            raise ValueError(f"{what} has an empty segment: {text}")
        return segments

    def matches(rule: str, path: str) -> bool:
        path_segments = split_strict(path, "path")
        rule_segments = split_strict(rule, "rule")

        if not rule_segments or rule_segments[0] == "!":
            # Drop rule
            for i in range(min(len(path_segments), len(rule_segments))):
                if rule_segments[i] != "*":
                    if path_segments[i] != rule_segments[i]:
                        return False
            if len(rule_segments) > 1:
                return True
        else:
            # Keep rule
            for i in range(len(rule_segments)):
                if rule_segments[i] == "*":
                    break
                elif rule_segments[i] != path_segments[i]:
                    return False
            return True

    # Validate every rule and path with split_strict, then keep each
    # path the last matching rule allows; a path no rule matches survives.
    filtered_listing = [path for path in listing if any(matches(rule, path) for rule in rules)]
    return filtered_listing
```