Grin of Audacity
An athlete in a race, an adventurer on top of a train, a Pirate boarding a ship, a cunning politician executing an amazing plan, a Loveable Rogue during a Sword Fight, a warrior during a Last Stand, two friends sparring—anyone facing an interesting and fun challenge with a reasonable chance of failure will sport one of these smiles. It's usually a bit forced, showing the strain and stress the user is under, and a there's certain edge of malice and aggressiveness to it, even insanity: a hint of Blood Lust, to be precise. It's very common against AntiHeroes type IV and V, especially if they are young and/or adrenaline junkies. It is usually coupled with a steady gaze, even a frown of sorts.
The heroic counterpart to the Slasher Smile and the Psychotic Smirk, which are mostly about enjoying the anticipation of hurting others, especially when it's secret and they're unaware of the threat. In contrast, the Grin of Audacity is about relishing the anticipation of winning. Very un-professional and un-business like, since it shows lack of emotional restraint, and comes more easily to Chaotic than to Lawful characters: don't expect characters modelled after serious-minded, saint-like, statuesque, iconic Superman or Batman to sport it often if at all: the heroes wearing these are supposed to be more sympathetic and human. Before the fear and the threats that a hero confronts, there are many ways one would realistically react, and this is one of them: If you've gotta do it, you might as well enjoy it.
Animated Films
- The Lion King: there's that scene with "I walk on the wild side...I laugh in the face of danger ha ha ha ha!" First it's young Simba, then Nala does it right before the big battle at the end.
- Eugene in Tangled wears this as he tries to speak an apology to Maximus before riding to Rapunzel's rescue.
Anime and Manga
- Tengen Toppa Gurren Lagann delivers some particularly compelling examples.
- In Magical Girl Lyrical Nanoha Striker S, Jail Scaglietti laughs when Fate finally captures him after years of pursuit.
- In Bleach this is pretty much the only time Ichigo smiles (apart from when he's extremely upset).
Comic Books
- The Flash is prone to these, at least the DCAU version.
- So are many Robins and Batgirl in the Batman family. Usually: in their case, it's youthful enthusiasm, insecure optimism, and a bit of a prankster spirit.
- And then there's some of Frank Miller's All Star Batman, when it isn't an outright slasher grin. Frank Miller is very fond of this trope in general. Sin City and 300 had many of those, and the movies even more so. Even when heroic, his characters tend to be on the bloodthirsty, violent side: aggressiveness is the key point here, and showing they are unscrupulous heroes.
Fanfic
- In Harry Potter and the Methods of Rationality's fan art, Harry is often represented wearing this, as befits a Young Conqueror, as do his retainers in the Chaos Legion (don't ask). Then a certain Wham! Episode happens, some illusions are shattered, and Harry's expressions become much more grim: it's instead Hermione and her group that take up most of the more optimistic kind of heroing.
Film
- Pirates of the Caribbean: "Now bring me that horizon!" Captain Jack Sparrow is very excited he got his ship back.
- The Mask in his movie and cartoon version tends to wear a more overjoyed, confident version of this. The anticipation isn't of effort, but of immense fun. By the end of the film, Ipkiss wears it a couple of times to signify he Took a Level in Badass.
- Traditionally associated with St Trinian's, which is almost entirely populated by female Loveable Rogue types, ever since the time of the founder Fritton, who was a Loveable Rogue himself. He was also William Shakespeare. And, he was a woman.
Literature
- Cyrano De Bergerac's various incarnations often wear this.
- Morgan and Derry exchange wicked grins in Deryni Rising just before Morgan secretly uses his powers to give a Connaiti mercenary his comeuppance.
Live Action TV
- On Glee, this is the typical expression worn by characters during uplifting songs, especially Barbara Streisand-style songs about extremely ambitious and extremely insecure characters.
Western Animation
- In My Little Pony Friendship Is Magic, this is Rainbow Dash's signature expression, though nearly all the mane cast has sported it in one occasion or another (such as Twilight during her In the Name of the Moon World of Cardboard Speech to Nightmare Moon... though, funnily enough, you can see her break her gaze as she's looking for the right words, the speech being improvised). Except Shrinking Violet Fluttershy, she's so nice you need Mind Control to get that expression out of her. In the case of Rainbow Dash, the insecurity angle is very very present: she's very boastful and aggressive, but she's also extremely sensitive about losing and failure.
- In The Powerpuff Girls, Blossom tends to range between this and your average benevolent smile, while Buttercup the Perpetual Frowner ranges between this and an outright scowl.
Video Games
- Sora when he stabs himself in the chest with the dark Keyblade to release Kairi's heart in Kingdom Hearts.
- In Katawa Shoujo, athlete Emi wears this expression when she's running, and the protagonist describes it in great length, as he finds that change from her standard, softer expressions fascinating.