Ryan Howard is one character on The Office who went through one of the more severe arcs in the series. From starting the series as a temp to reaching his peak when he got a job at corporate, everything for Ryan fell apart when he went to jail. It’s not until Michael hired him at the Michael Scott Paper Company that Ryan was given a second chance.
Aside from his job at Dunder Mifflin and Sabre, Ryan’s relationship with Kelly Kapoor also had a transformation. The same can be said for his sense of style and personality shifts. From season 1 onward, Ryan had quite a transformation over the years.
Season 1: Quiet And In The Background
The one thing that season 1 of The Office did well was keep audiences engaged with the ups and downs of office life, which wasn't easy. Since the first season only had six episodes, the writers had to keep viewers interested in the lives of Dunder Mifflin employees.
With the first season being so short, Ryan's main role was being a hardworking temp in an office of older individuals who had been at the company for years. In the episode "The Alliance," Ryan got lucky when the branch wasn't downsized and he could continue working there.
Season 2: Serious About His Future
In season 2, Ryan was still at business school and made a point that he wanted to continue gaining knowledge of business life so that he could one day run his own business. However, it didn't make much sense that Ryan continued being a temp at a failing paper company when he assumed he was capable of so much more.
In season 2, he set an accidental fire in the office when he burned his lunch, but he also started a romantic relationship with Kelly Kapoor with a little nudge from Jim. This was the start of Ryan's rocky relationship with Kelly as he tried to figure out what kind of future he wanted with the company.
Season 3: Two Promotions & A Bright Future
At the start of season 3, Ryan was promoted from temp to a full-time sales position when Jim left the Scranton branch for Stamford. Ryan was excited for his new role at Dunder Mifflin but wasn't great at sales, which is when Dwight tried to give him a lesson the hard way.
At the end of season 3, Ryan's life changed forever when he was promoted from sales to a corporate position in New York. One of the final scenes was Ryan dumping Kelly because he was ready for an exciting start in the Big Apple.
Season 4: A Life In Manhattan & Jail Time
In the fourth season, the Scranton branch had to get used to Ryan's new leading role within the company. Michael and Jim couldn't treat him the same way as if he were still a temp because now he had the ability to fire them. Ryan transformed into a corporate-looking guy with slicked hair, a goatee, and nice suits.
To many, Ryan was the worst in season 4 because of the power trip he was on. His role at corporate was to create Dunder Mifflin Infinity — Dunder Mifflin's interactive website where sales could be done online. However, there were a ton of problems with his website, which resulted in Ryan committing fraud, being arrested, and losing his job.
Season 5: Temp Life
After being released from prison, Michael re-hired Ryan at Dunder Mifflin as a temp (yet again). Ryan still had his ego from the prior season but had no leverage to do anything permanent to those who wronged him.
Ryan tried getting back together with Kelly but she chose Darryl... at least for a short time. However, Ryan and Kelly did eventually get back together. As much as Ryan was at his peak in season 4, he was at his lowest in season 5. He eventually started working at a bowling alley before joining The Michael Scott Paper Company and getting his temp job back at Dunder Mifflin. In short, season 5 was a whirlwind for Ryan's career and ego.
Season 6: A New Hipster Attitude
In the sixth season, Ryan completely transformed into a know-it-all who bothered everyone in the office. More than that, he changed his appearance and personal style to reflect the new persona he was trying to emulate.
Instead of focusing on business, Ryan started dabbling in photography and finding get-rich-quick schemes, like his new website WUPHF.com. By the end of the season, he tried his best to bug Jim as payback for how Jim treated him when he went to jail. Season 6 proved how much Ryan changed in The Office.
Season 7: WUPHF.COM
After mentioning WUPHF.com in season 6, Ryan's vision came to life in season 7 as he tried to get funding from his coworkers. However, without a proper business plan, he was encouraged to sell his website to Washington University Public Health Fund (WUPHF) to get his colleagues' money back.
When Micahel left Dunder Mifflin and Deangelo took his place as the boss, Ryan wanted to make a good impression, so he lied and said he was Kelly's boss instead of the other way around. Rather than being a more open and truthful worker, Ryan's personality remained corrupt.
Season 8: A Trip To Tallahassee
When Robert California became the CEO, Ryan tried his best to show off his business ideas but it didn't go the way he expected. However, when there was an opportunity to go on a work trip to Tallahassee, Ryan jumped at the opportunity.
However, when Ryan was given the chance to do an in-depth presentation of the Sabre Pyramid, he flaked and couldn't go through with it. Considering it was season 8, it was surprising that Ryan didn't learn from his mistakes and flourish.
Season 9: A Move To Ohio And A Baby
In season 9, Ryan shut down when he came back from Florida and realized Kelly was in love with another man. When Kelly admitted she was quitting her job to move to Ohio for her relationship, Ryan also quit to follow her.
Ryan didn't make an appearance again until the end of the season at Dwight's wedding. As it turned out, Ryan had a son named Drake. Ryan was still single and Drake's mom was not involved in their lives, so he shot his shot with Kelly yet again. The last viewers saw Ryan, he was running off into the sunset with Kelly, after leaving his son with Kelly's (now) ex-fiancé. It was one of Ryan's cringiest moments because he didn't mature at all by the end of the series.