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


def prune_listing(listing, rules):
    def segment_fits(pattern, text):
        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, what):
        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

    # Validate every rule and path with split_strict, then keep each
    # path the last matching rule allows; a path no rule matches survives.
    pruned_list = []
    for path in listing:
        matched = False
        for rule in rules:
            segments = split_strict(path, "path")
            rule_segments = split_strict(rule, "rule")
            if rule_segments[0] == "!":
                matched = True
            else:
                for i, rule_segment in enumerate(rule_segments):
                    if i >= len(segments) or segments[i] != rule_segment:
                        matched = False
                        break
            if matched:
                pruned_list.append(path)
                break
    return pruned_list
```