In order to understand in what order to watch Kimagure Orange Road, you must first understand what it is. Kimagure Orange Road had its first manga volume printed in March 26 1984, a time when mangas and animes were mostly composed of standalone episodes. Even though there was an overarching theme or plot throughout the series, in this case it is the development of the love triangle between the main characters, the longest story arcs last three to five volumes at most, meaning that each volume initiated and concluded its main plot. This was also reflected in the anime series at the time.
Kimagure Orange Road is one of the most important animes of all time as it set the standards for what a romantic comedy shounen is. Many of the archetypes of this anime are seen even until today in animes of the same genre. It introduced the concept of a time loop (which today it can still be seen in animes like The Melancholy of Haruhi Suzumiya, and Rascal Doesn’t Dream of Bunny Girl Senpai) and debatably the concept of what a tsundere girl is (along with Urusei Yatsura). It was also one of the first animes to portray a love triangle as the main plot and to introduce the element of the supernatural in a romantic shounen which inspired a whole genre of romantic animes which is still ongoing today (Your Name, Weathering With You and Monogatari Series are some examples).
Most importantly, this anime is a sign of its time. Kimagure Orange Road is without a doubt the Grease and Saturday Night Fever of anime.
It portrays Japanese youth culture during the 1980s as well as what was happening in Japan and around the world at the time, from the clothes they wear, the activities they do (such as illegally going to clubs, pilates, starting a rock band, hanging out in coffee shops etc.) their interests and even the way they talk. One could compare watching Kimagure Orange Road to watching American teen comedy movies from the 80s such as The Breakfast Club, Sixteen Candles, and other movies of the likes. Kimagure Orange Road will mostly give the viewer a taste of what Japanese life was like back in the day, particularly for the youth, with all its city pop music and the aesthetic visuals, which their appretiation is coming back to life in many social media platforms such as tumblr and pinterest.
Without more to say, this is the order to watch Kimagure Orange Road:
Anime Television Series: Episode 1 – 24.
Movie: Shonen Jump Special: Kimagure Orange Road
Anime Television Series: Episode 25 – 33
OVA: White Lovers
OVA: Hawaiian Suspense
Anime Television Series: Episode 34 – 42
OVA: I was a Cat, I was a Fish
OVA: Hurricane! Akane the Shape-changing Girl
OVA: Stage of Love=Heart on Fire! Spring is for Idols
OVA: Stage of Love=Heart on Fire! Birth of a Star
Anime Television Series: Episode 43 – 46
OVA: An Unexpected Situation
OVA: Message in Rouge
Anime Television Series: Episode 47 – 48
Movie: I Want to Return to that Day
Movie: Shin Kimagure Orange Road: Summer’s Beginning