Yoshi’s Story: Bowser I born. Yoshi’s Island: Mario and Luigi born. Yoshi’s Island 2: Peach, DK, Wario, Daisy, pretty much every other character born.
Mario and Luigi Parners in Time: The past part of this game happens somewhere around this point. Punch-Out!!, Wrecking Crew, Alleyway, Golf, Tennis, etc: A lot of time passes, Mario gets a lot of refereeing and blue collar jobs to make ends meet. Donkey Kong ‘94: During another menial construction job, Mario chases a giant ape through the city, the jungle, and ends up in the Mushroom Kingdom. This game replaces the events of Donkey Kong and Donkey Kong Jr. Mario Bros.: Mario reunites with Luigi. Super Mario Bros.: Mario rescues Peach from Bowser I. Super Mario 64: Peach invites Mario to her castle to thank him for the rescue. Super Mario Sunshine: To thank Mario for another rescue, Peach takes him on vacation with her. Between this and SM64, Bowser Jr. (Bowser II) born. New Super Mario Bros.: As part of Bowser II’s training, Bowser I decides to re-enact the events of Super Mario Bros. Super Mario Land: To thank Mario for yet ANOTHER rescue, Peach gives Mario lordship over a section of land, hereby known as Mario Land. Rescues princess of nearby Sarasa Land. Super Mario Land 2: While distracted by the events of Super Mario Land, Wario takes over Mario Land and its respective castle. Super Mario Galaxy: Bowser I, who is getting old, makes one last grand attempt to take over the universe. Mario meets yet another princess. Mario Land destroyed, and Mario forced to live in a much smaller house. Super Mario RPG: At this point, Bowser I is just going through the motions. With Bowser II grown up and out of the castle, Bowser I passes time by kidnapping Peach, sparring with Mario, and then teams up with him to protect his legacy. Rumors spread of Mario’s jumping abilities in Galaxy; everyone believes he can jump from planet to planet. Super Mario Bros. 2: Following the crazy events of Galaxy and RPG, Mario is forced to ponder the complexities of time, space, and his own existence, and has a messed up dream. Luigi’s Mansion: I never played Luigi’s Mansion, but apparently there’s an appearance by a deceased Bowser that is most likely Bowser I. Bowser II inherits Koopa empire. Super Mario Bros. 3: Between this game and Luigi’s Mansion, Bowser II has 7 kids, who are all indoctrinated in the family’s “kidnap the princess” business. Super Mario World: Mario decides to finally visit his “birthplace”, Yoshi’s Island. Bowser II, having never been there either, decides to follow him. Both are completely disappointed by the lack of Shyguys. Mario and Luigi: By this point, Mario is one of the most famous figures in this world; Luigi’s doing well enough too. In this game, there’s a museum of all the past blocks. Mario and Luigi Parners in Time: This is where the present part of the game is. Sports/Kart games: Using the time machine from Partners in Time, Mario’s able to re-unite with all his past friends and foes, including the late Bowser I, all with the purpose of playing soccer, golf, and racing go-karts. A total waste of resources, but Mario’s probably a billionaire by this point.