Tunnels & Trolls solved this problem with the attribute-based "saving roll," which enabled player-characters not only to avoid certain death in the manner of the D&D saving throw, but to take risky moves to gain an advantage in a fight or perform other feats. This game mechanic depends on dynamic attribute ratings that have no upper limit, and it would be simpler just to play T&T than adapt its rules to a game such as D&D. This is actually an excellent idea for anyone who wants to play a swashbuckling role-playing game. Just strip out the fantasy elements (or keep some if you want to play a fantasy swashbuckling game in the spirit of, say, the Sinbad movies) and T&T will probably serve you well in conveying that cinematic swashbuckling action.
D&D played as written tends to reward caution, not derring-do. This doesn't prevent us from tinkering with it, though, in the hopes of transforming it into a game worthy of the exploits of Errol Flynn. One of my untested ideas is simply to import the Fudge rules of action resolution and apply them to the standard D&D attributes. Convert the attributes to the Fudge trait ladder, then whenever a player character wants to try something crazy, the referee determines how difficult it is and the player rolls four Fudge dice per the standard rules for an unopposed roll. If the result is equal to or greater than the difficulty level, then the player character accomplishes the stunt. When an attack is made, revert to the D&D rules, modified by a suitable bonus or penalty depending on whether the stunt succeeds or fails (if appropriate). The conversion I use for the 3-18 range is as follows:
18 | Superb |
16-17 | Great |
13-15 | Good |
9-12 | Fair |
6-8 | Mediocre |
4-5 | Poor |
3 | Terrible |
For those who don't like the idea of inflating the importance of the existing attributes, a seventh attribute (called "swashbuckling" perhaps) could be added. It could be generated in the same manner as the usual attributes (3d6, 4d6 drop lowest die, or whatever), converted to the Fudge trait ladder, and used as above.
I have yet to playtest any of this, so use at your own risk...