So it dawned on me that this list is out of date by a good eight years (!)
That was a crazy time, reviewing a movie a day. I have no idea how I had the energy to do that haha.
That said, here is my updated and revised list as of today, April 24th, 2018, which with the sheer volume of comic book films we've had since has bulked up from 100 to a staggering 161 titles...and it's only what I've seen, not exactly EVERY comic book or superhero film ever made. Several films, most obviously the majority of the MCU and all the DCEU, have been added and given changing tastes, some of the order has shifted around a little:
1. Superman: The Movie (Richard Donner, 1978)
2. The Dark Knight (Christopher Nolan, 2008)
3. Batman: Mask of the Phantasm (Bruce W. Timm and Eric Radomski, 1993)
4. Batman (Tim Burton, 1989)
5. Captain America: The Winter Soldier (Joe and Anthony Russo, 2014)
6. Superman II (Richard Lester, 1980)
7. X2: X-Men United (Bryan Singer, 2003)
8. The Avengers (Joss Whedon, 2012)
9. Blade (Stephen Norrington, 1998)
10. Batman Begins (Christopher Nolan, 2005)
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11. Spider-Man II (Sam Raimi, 2004)
12. Captain America: Civil War (Joe and Anthony Russo, 2016)
13. Logan (James Mangold, 2017)
14. Iron Man (Jon Favreau, 2008)
15. The Crow (Alex Proyas, 1994)
16. Batman: The Dark Knight Returns (Jay Oliva, 2012/2013)
17. Road to Perdition (Sam Mendes, 2002)
18. The Dark Knight Rises (Christopher Nolan, 2012)
19. X-Men: Days of Future Past (Bryan Singer, 2014)
20. Watchmen (Zack Snyder, 2009)
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21. Sin City (Robert Rodriguez and Frank Miller, 2005)
22. Spider-Man (Sam Raimi, 2002)
23. X-Men (Bryan Singer, 2000)
24. Batman Beyond: Return of the Joker (Curt Geda, 2000)
25. Avengers: Age of Ultron (Joss Whedon, 2015)
26. Black Panther (Ryan Coogler, 2018)
27. Wonder Woman (Patty Jenkins, 2017)
28. Superman Returns (Bryan Singer, 2006)
29. Teenage Mutant Ninja Turtles (Steve Barron, 1990)
30. Wonder Woman (Lauren Montgomery, 2009)
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31. The Incredibles (Brad Bird, 2004)
32. Batman v Superman: Dawn of Justice (Zack Snyder, 2016)
33. Spider-Man: Homecoming (Jon Watts, 2017)
34. Deadpool (Tim Miller, 2016)
35. Guardians of the Galaxy (James Gunn, 2014)
36. Batman: Under the Red Hood (Brandon Vietti, 2009)
37. Thor: Ragnarok (Taika Waititi, 2017)
38. Big Hero 6 (Don Hall & Chris Williams, 2014)
39. Doctor Strange (Scott Derrickson, 2016)
40. Blade II (Guillermo Del Toro, 2002)
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41. Batman Forever (Joel Schumacher, 1995)
42. The Rocketeer (Joe Johnston, 1991)
43. Batman Returns (Tim Burton, 1992)
44. Captain America: The First Avenger (Joe Johnston, 2011)
45. The Wolverine (James Mangold, 2013)
46. All-Star Superman (Sam Liu, 2011)
47. Justice League: Crisis on Two Earths (Lauren Montgomery and Sam Liu, 2010)
48. X-Men: First Class (Matthew Vaughn, 2011)
49. Man of Steel (Zack Snyder, 2013)
50. Justice League: The Flashpoint Paradox (Jay Oliva, 2013)
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51. Iron Man III (Shane Black, 2013)
52. Guardians of the Galaxy Vol. 2 (James Gunn, 2017)
53. Superman/Batman: Apocalypse (Lauren Montgomery, 2010)
54. Batman: Year One (Lauren Montgomery and Sam Liu, 2011)
55. Ant-Man (Peyton Reed, 2015)
56. Justice League (Zack Snyder/Joss Whedon, 2017)
57. The Incredible Hulk (Louis Leterrier, 2008)
58. The Lego Batman Movie (Chris McKay, 2017)
59. Justice League: Gods and Monsters (Sam Liu, 2015)
60. Batman & Mr. Freeze: Sub Zero (Boyd Kirkland, 1998)
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61. Superman/Batman: Public Enemies (Sam Liu, 2009)
62. The Mask (Chuck Russell, 1994)
63. Batman: Mystery of the Batwoman (Curt Geda, 2003)
64. Green Lantern: First Flight (Lauren Montgomery, 2009)
65. Superman vs. The Elite (Michael Chang, 2012)
66. Batman: The Movie (Leslie H. Martinson, 1966)
67. Conan The Barbarian (John Milius, 1982)
68. Suicide Squad (David Ayer, 2016)
69. Daredevil (Mark Steven Johnson, 2003)
70. X-Men: Apocalypse (Bryan Singer, 2016)
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71. Batman vs. Robin (Jay Oliva, 2015)
72. Spider-Man III (Sam Raimi, 2007)
73. Iron Man II (Jon Favreau, 2010)
74. Justice League: Throne of Atlantis (Jay Oliva and Ethan Spaulding, 2015)
75. The Mask of Zorro (Martin Campbell, 1998)
76. The Punisher (Jonathan Hensleigh, 2004)
77. Superman: Doomsday (Bruce W. Timm, Lauren Montgomery and Brandon Vietti, 2007)
78. Batman: Bad Blood (Jay Oliva, 2016)
79. Constantine (Francis Lawrence, 2005)
80. Hellboy II: The Golden Army (Guillermo Del Toro, 2008)
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81. Punisher: War Zone (Lexi Alexander, 2008)
82. Thor (Kenneth Branagh, 2011)
83. Justice League: War (Jay Oliva, 2014)
84. The Shadow (Russell Mulcahy, 1994)
85. Kick-ash (Matthew Vaughn, 2010)
86. V for Vendetta (James McTeigue, 2006)
87. Hulk (Ang Lee, 2003)
88. Justice League: Doom (Lauren Montgomery, 2012)
89. Teenage Mutant Ninja Turtles II: The Secret of the Ooze (Michael Pressman, 1991)
90. Hellboy (Guillermo Del Toro, 2004)
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91. The Amazing Spider-Man (Marc Webb, 2012)
92. 300 (Zack Snyder, 2007)
93. Batman: The Killing Joke (Sam Liu, 2016)
94. Son of Batman (Ethan Spaulding, 2014)
95. Blade: Trinity (David S. Goyer, 2004)
96. Planet Hulk (Sam Liu, 2010)
97. Justice League vs Teen Titans (Sam Liu, 2016)
98. Darkman (Sam Raimi, 1990)
99. Dredd (Pete Travis, 2012)
100. Mighty Morphin Power Rangers: The Movie (Bryan Spicer, 1995)
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101. Batman: Assault on Arkham (Jay Oliva and Ethan Spaulding, 2014)
102. X-Men: The Last Stand (Brett Ratner, 2006)
103. Ghost Rider: Spirit of Vengeance (Neveldine & Taylor, 2012)
104. The Amazing Spider-Man II (Marc Webb, 2014)
105. Thor: The Dark World (Alan Taylor, 2013)
106. Fantastic Four (Josh Trank, 2015)
107. Superman: Unbound (James Tucker, 2013)
108. 300: Rise of an Empire (Noam Murro, 2014)
109. Avengers Confidential: Black Widow & Punisher (Kenichi Shimizu, 2014)
110. Doctor Strange: The Sorcerer Supreme (Jay Oliva, Patrick Archibald and Richard Sebast, 2007)
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111. Kick-ash 2 (Jeff Wadlow, 2013)
112. Mystery Men (Kinka Usher, 1999)
113. Thor: Tales of Asgard (Sam Liu, 2011)
114. Fantastic Four: Rise of the Silver Surfer (Tim Story, 2007)
115. TMNT (Kevin Munroe, 2007)
116. Ghost Rider (Mark Steven Johnson, 2007)
117. Fantastic Four (Tim Story, 2005)
118. Conan The Destroyer (Richard Fleischer, 1984)
119. The Spirit (Frank Miller, 2008)
120. Superman III (Richard Lester, 1983)
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121. Batman & Robin (Joel Schumacher, 1997)
122. The Punisher (Mark Goldblatt, 1989)
123. Superman and the Mole Men (Lee Sholem, 1951)
124. Sin City: A Dame to Kill For (Robert Rodriguez and Frank Miller, 2014)
125. The Batman vs Dracula (Michael Goguen, 2005)
126. The Phantom (Simon Wincer, 1996)
127. Spawn (Mark A.Z. Dippé, 1997)
128. Teenage Mutant Ninja Turtles (Jonathan Liebesman, 2014)
129. Teen Titans: Trouble in Tokyo (David Slack, 2006)
130. Ultimate Avengers: The Movie (Curt Geda and Steven E. Gordon, 2006)
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131. Superman: Brainiac Attacks (Curt Geda, 2006)
132. X-Men Origins: Wolverine (Gavin Hood, 2009)
133. The Green Hornet (Michel Gondry, 2011)
134. Green Lantern (Martin Campbell, 2011)
135. Captain America (Albert Pyun, 1990)
136. Ultimate Avengers II: Rise of the Black Panther (Will Meugniot and Richard Sebast, 2006)
137. The Incredible Hulk Returns (Nicholas J. Corea, 1988)
138. Swamp Thing (Wes Craven, 1982)
139. Supergirl (Jeannot Szwarc, 1984)
140. Judge Dredd (Danny Cannon, 1995)
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141. Elektra (Rob Bowman, 2005)
142. The Return of Swamp Thing (Jim Wynorski, 1989)
143. Teenage Mutant Ninja Turtles III (Stuart Gillard, 1993)
144. Darkman II: The Return of Durant (Bradford May, 1995)
145. Captain America II: Death Too Soon (Iván Nagy, 1979)
146. The League of Extraordinary Gentlemen (Stephen Norrington, 2003)
147. Barb Wire (David Hogan, 1996)
148. The Crow: City of Angels (Tim Pope, 1996)
149. Nick Fury: Agent of S.H.I.E.L.D. (Ron Hardy, 1998)
150. Darkman III: Die Darkman Die (Bradford May, 1996)
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151. Jonah Hex (Jimmy Hayward, 2010)
152. Captain America (Rod Holcomb, 1979)
153. The Crow: Wicked Prayer (Lance Mungia, 2005)
154. Catwoman (Pitof, 2004)
155. Tank Girl(Rachel Talalay, 1995)
156. Steel (Kenneth Johnson, 1997)
157. Man-Thing (Brett Leonard, 2005)
158. Son of the Mask (Lawrence Guterman, 2005)
159. Howard The Duck (Willard Huyck, 1986)
160. The Fantastic Four (Oley Sassone, 1994)
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161. Superman IV: The Quest for Peace (Sidney J. Furie, 1987)