Michael Scott was a complex character who showed his true colors over time. In the first season, he was incredibly offputting and didn't show an ounce of redeeming qualities. But as the series went on, a softer side of Michael emerged. Sure, he said outlandish things and interrupted the workday on a daily basis but deep down was a man who cared.
Michael left Scranton in season 7 to start a new life in Colorado with his fiancée, Holly. The Scranton branch hurried to find a new regional manager that had the same outlook as Michael Scott but it was impossible. He popped up in the series one last time in the series finale at Dwight and Angela's wedding, giving The Office fans all the feels. He certainly has transformed since season 1.
Season 1: Slicked Hair & Tight Collars
Michael Scott in season 1 looked and acted completely different than other seasons. It's obvious that the show was trying to figure out Michael's look and how his employees responded to his eccentric behavior.
Aesthetically, Michael's hair was slicked back, which made him look more intimidating than he actually was. He also wore a lot of white shirts (sans jacket) that looked tight around his neck. Michael looked, in a word, stuffy. He still acted as he did throughout the series but he was less empathetic.
Season 2: New Hair & More Personable
Season 2 did an entire revamp on Michael's character. Physically, he appeared more approachable and less threatening. After all, Michael is anything but a menacing character. He's simply naive and wants people to like him.
Michael also became more personable in season 2. Viewers saw his brotherly relationship with Dwight develop (especially in "The Fight") and his sympathetic side in "Booze Cruise." It became obvious in this season that his employees cared for him but didn't always trust him.
Season 3: Side Part & Job Changes
By season 3, Michael finally found the hairstyle that he'd stick with throughout his time on the series: a side part. It was relaxed and free of the thick gel he wore in the first season. Style-wise, Michael stuck with suits when in the office setting but let loose in episodes like "Beach Games," "The Convention," and "Cocktails."
It's in this season that Michael finally lands the woman of his dreams: Jan Levinson. After flirting with her since the first season, his charms finally paid off when he and Jan went to Jamacia together. From then on, Jan couldn't deny her feelings for him and they started their toxic partnership.
Season 4: In Shape & Finding Himself
Michael looked toned and in shape by season 4 of The Office. According to the Office Ladies podcast, Steve Carell got into great shape off-camera for his role in The 40-Year-Old Virgin and kept up with his fitness regimen afterward. On The Office, Micahel was finally in a serious relationship, had a good job, and life was seemingly good.
Sadly, by the time "Dinner Party" came around, Michael's happiness faded. He was in mounds of debt and his relationship was no longer serving him. While he never looked better physically, his home life was a mess.
Season 5: Facial Hair & Changing It Up
By the start of season 5, Michael had a crush on the new human resources rep, Holly, but was in a complex and fictional relationship with Jan's upcoming baby. Michael was not the father of Jan's baby but somehow wanted the responsibilities of the baby's father. While Michael still acted irrationally and without thought, he was slowly maturing.
He and Holly started a relationship before she transferred branches, and it took him the entire season to get over her. By the time "Company Picnic" rolled around, viewers saw a new mature side to Michael as he told cameras that he was not in a rush to win back her heart. Business-wise, Michael left Dunder Mifflin to start the Michael Scott Paper Company, which totally shifted his priorities.
Season 6: Confidence Is Key
In the sixth season, Michael is back with Dunder Mifflin and on a new path. He's thankful to be in the office with the people he loves and was hopeful. He started dating Pam's mother, Helene, in season 6, which caused a rift between him, Pam, and Jim, but that relationship fizzled out as quickly as it started. Michael later began a relationship with a married woman named Donna. He had this outward confidence that his employees didn't quite understand but he pulled it off.
Season 7: Same Look, New Path
Michael's appearance on the outside stayed relatively the same but emotionally, Michael had changed by season 7. He was getting older and ready for a family; he was tired of being alone. Michael and Holly finally got back together in this season, which was the reason behind him leaving Dunder Mifflin forever. It was an incredibly hard decision for Michael because he was comfortable in Scranton and loved his employees, but a new life in Colorado awaited him. His last appearance was in "Goodbye, Michael." Dunder Mifflin was left with picking up the pieces and finding someone to take his place.
Season 9: Grey & Happy
Michael made one last appearance in the series finale. It was a shock to everyone at Dwight and Angela's wedding, and to viewers. Michael surprised Dwight as his best man and was thrilled to see his old friends again. He was tan, a little grey in the hair, but ultimately looked happy and healthy. He and Holly were now married and had four children together. He told Pam that he bought two cell phones just to store all of the pictures he took of them. Although it was sad to not have Michael at Dunder Mifflin anymore, he was living his best life in a new state.