The No More Heroes series is full of phenomenal boss fights. Really, that is a large part of why the series has such an established cult-following. I love both of the games and the assassins Travis faces throughout them, but as this is a top five list, I can only include my very favorites from the lot. Let the bloodshed begin!
#5 - Margaret Moonlight: The fight against Margaret is largely a test of your ability to adjust your strategy on-the-fly. When she's at a distance, she'll hit you hard with shells from her guns. Blocking these will quickly deplete the charge of Travis' beam katana, and he will have to find some cover in order to recharge. The catch is that the surrounding environment is destructible, and Margaret will continue moving about. When Travis does manage to get close enough to land some direct hits with his beam katana, Margaret goes on the defensive, blocking strikes and then performing flips to not only dish some damage Travis' way but also to knock him back a fair distance, which will allow her to once again fire upon him.
#4 - Jeane: Though not officially ranked with the UAA, Jeane puts up one of the best fights of anyone between the two No More Heroes titles. Because a fight is exclusively what the boss encounter with Jeane is all about - she uses her endurance to kick, punch, and dodge Travis' beam katana. The fight can last a decent amount of time, due simply to the fact that her later attacks are carried out in rapid succession. Jeane knows exactly what she is getting herself into the moment she interrupts Travis' exchange with Dark Star, and is prepared to go all-out, giving Travis the fight of his life.
#3 - Holly Summers: A lethal beauty, Holly relies on explosives and the art of deception to try and best Travis. Approaching her will lead Travis to fall into a pit... time and time again. If he does not climb out quickly enough, he will get an up-close-and-personal visit from a hand grenade. When Holly loses this advantage, she launches a barrage of missiles Travis' way, forcing him to duck and roll one way or the other, and subsequently providing Holly time to either move or draw forth her shovel for close-quarters combat.
#2 - Harvey Moiseiwitsch Volodarrskii: Flashy, flamboyant - some might even say fabulous - Harvey uses his mastery of theatrics and magic to mess with both Travis and the player. He regularly performs disappearing acts, inverts both the stage and Wiimote controls, and deals some damage to Travis by trapping him inside a box. The encounter is very much unorthodox, but the quirky theatrical immersion it presents proves far more entertaining than frustrating.
#1 - Alice Twilight: There are a few fights, like those against Skelter Helter and Ryuji, that pit Travis against another beam katana-wielding foe. But both of those assassins rely rather heavily on ranged attacks - the former with his gun and the latter with his summoned dragon. Alice Twilight provides the closest thing Travis gets to a real one-on-one battle between two masters of the beam katana. Yes, there was that battle with Henry at the end of the original No More Heroes, but considering it is a post-game treat and insanely difficult, I don't feel it has the same qualifications as most other boss fights. Kimmy Howell used a dual-bladed beam katana, but she was a silly schoolgirl who thought she was stronger than she truly was.
Alice Twilight, on the other hand, knows exactly what she is getting herself into the moment Travis arrives to challenge her. She knows her strengths and weaknesses, and though she can launch her blades a short distance, she plays a mostly defensive game, hoping to lure Travis in and then dropping down to strike at him. Her arsenal is simple, but effective, and looks radical to boot.