If you ask the cinema buff in me, then its no contest. Rocky 1 was far and away the best movie of the series. But for pure entertainment and rewatch value, Rocky III is the most fun film of the series IMO. IV was also fun and iconic, but the franchise went to shit after that and I haven't enjoyed any Rocky film since IV.
Rocky I - Far and away the best movie of them. Sure the story is a big cliche and unbelievable at that but Stallone's acting and some good writing make it a sports movie classic. Rocky II - By art standards obviously the second best of the series. However the storytelling is dragging and the end is visible from the start (I mean, how else could the story continue). Very little rewatchability. Rocky III - Difficult to compare to the first two as it is basically a comedy movie with very little logic. Still, I rewatch it every now and then, unlike the second, and Mr T is a great villain. Rocky IV - If possible, even more corny than the third with the robot and everything. The movie is almost a musical with several songs played during it, obviously just to make the film last over an hour. Still, the training scenes are still inspiring, I still want to hit the gym whenever I watch them. Rocky V - From comedy to a tragedy in every sense of the word. Despicable movie in every way. Rocky Balboa - Better than the fifth but almost plotless with Rocky walking around for 90 minutes mumbling nonsense and having a meaningless fight. Creed I - Had it been a new movie idea, it would have been excellent with a charismatic young lead and Stallone playing a good mentor, which doesn't really make sense considering how dumb the character has previously been. Now, it was one in a dozen Hollywood film Creed II - Bit better than the first. It had the same idea as the Cobra Kai but not nearly as well and isn't unforgettable by any means
III & IV weren't good movies, but the point is they were FUN, and still rewatchable now. After IV, every Rocky film has been a dull melodrama. Like watching paint dry.
Rocky - No Explanation Needed... Rocky II - Drags a Bit, as UGO Stated, But a Logical Next Step in the Series... Rocky III - To Xplosive's Point, This is NOT a 'Good Movie', Per Se, But it's the Ultimate GUILTY PLEASURE Film...Is There a BETTER Opening Montage in Motion Picture History???... How Many People Were INITIALLY Attracted to Boxing by the Rocky III Opening Montage???...What Song Takes You from 0-60 QUICKER Than "Eye of the Tiger" Does???.... Creed - REED Expected to HATE Creed But Was Pleasantly Surprised...The Storyline was Formulaic Yet Stallone UPDATED It In an Entertaining, Believable Fashion... Rocky IV - Another Guilty Pleasure Film Which Unapologetically Pimped Out and Exploited the Cold War...Rewatchable, But THE Most Over-the-Top of All the "Rocky" Flicks... Creed II - A Bit RUSHED, But a Quality Film Nonetheless...The Boxing NERD In REED Always Wondered What Happened in the Fictional Life of Ivan Drago, Post-Rocky IV, and that Question Was Answered... Still, w/Creed Now Having Faced the Hulking, Vicious, Impenetrable, Revenge Fueled Son of Ivan Drago, WHO Does he Face in Creed III???...REED Thinks Andre Ward's Character Should've Been the MAIN Opponent in "Creed II", w/Drago's Son Being Slotted for "Creed III"... Now, Creed is Like Terence Crawford on a Top Rank Contract; No More CREDIBLE Opponents... Rocky Balboa - Hardest of All for REED to Watch, for Obvious Reasons...Stallone Hand Picked Roy Jones to Play "Mason Dixon", Roy KNEW This, Took his Sweet Time in Confirming His Involvement w/Sly, Got KTFO By Tarver in the Interim, and the Rest is Cinematic History... Decent Film Though...Admittedly, Tarver Has Better ACTING Chops Than Roy and the "Computer Fight" Angle was a Nice Homage to Boxing History...It Showed Even in the Exaggerated Life of His Fictional Alter-Ego, Stallone RESPECTED the Sport of Boxing... Rocky V - Morrison's "Heel" Turn was a Bit WWEish, the Don King Caricature Got Old QUICK and the CLIMAX was a Street Fight???...No Bueno!!!...In the 30 Years Since Rocky V was 1st Released, REED's Watched it from Start to Finish No More than 2wice... Muhammad Ali's INFLUENCE On the "Rocky" Series Can't Be Stressed Enough... Stallone was Intrigued by Chuck Wepner's Mob Related Back Story as he Challenged Ali for the Title...Of Course, Apollo Creed WAS Muhammad Ali and Mr. T. was a Celebrity Bodyguard Prior to Getting Into Film/TV, Most Notably FOR Muhammad Ali... REED Doubts Ali Got a Dime of the "Rocky" Proceeds But it's Doubtful the Project Itself EVER Gets Launched, Nevermind Sustains a Shelf Life Nearly Half a CENTURY Later, if Not for Him... REED