Guy called Five

It goes all the way back to the first episode when Ray hires Henry. He specifically says that he can't do this forever, that he needs help, and that he needs someone to take over for him. I start here, because this scene sets up a lot of Ray's mentality and progression. It shows his acknowledging how hard being Captain Man is, and that he's already thinking about not being Captain Man anymore. He's in his early thirties and is already thinking about retiring.

This is also the whole reason he hired Henry. To train him to take over as Captain Man, so that he can quit. Because Ray's entire life was consumed by Captain Man at the age of eight, even if Captain Man wouldn't exist for another ten years.

Ray and Captain Man are also a lot more distinct in the first two seasons and even into season 3. Ray is still very Ray, but there is a certain seriousness when he is in costume. The way he walks, talks, and interacts is different. There is a line between Ray and Captain Man.

There is also a line between Ray and Henry. While Ray cares about Henry in the first season, in the early episodes there is a distance. It makes sense, they're is a natural chemistry that makes them a great duo, but there's not the same emotional depth we see later. In Mo' Dangers Mo' Problems when confronted with Henry's issue of balancing life, Ray's solutions all center around fixing the problem so Henry has more time to be Kid Danger, not giving him more time off to better balance the two lives. Looking at it, Ray cares about Henry as his replacement.

I think this is prominent in The Secret Gets Out. He does not hesitate to fire Henry after Charlotte finds out. There is no tough goodbye, or back and forth. Just Ray firing Henry. The only reason Henry got his job back, was because of his very public and successful take down of Phoneshark, and to some degree Charlotte passing the test.

This theme continues in Jolly Beetle. Ray looses his powers and is ready to give up. Henry has a few months under his belt is holding down the fort, so Ray just gives up. It's not until Henry confronts Ray about wanting Captain Man, and specifically when he leaves to "Do [his] job," that any kind of regret or hesitance is shown by Ray.

He's trying to be better than his father, but ultimately he is training Henry to take over, not for them to be a duo forever. There is a certain professional distance between the two.

UNTIL CAVED IN

I really think this is where a huge shift happens in the dynamic between Henry and Ray. Ray has lived a very lonely existence. Practically no one knows his identity, there is a distinct separation between Captain Man and Ray, and his closest friend (Schwoz) stole his girlfriend and they weren't on speaking terms for years. Even then, when Ray is in a bad mood because of his super anniversary, everyone leaves to avoid it.

But Henry, he's willing to stay. Sees how hurt Ray is and does something about it. Even when the plans get derailed Henry makes the most of it. And Ray is genuinely touched, and surprised by the gesture. Henry isn't doing this for Swellview and it has nothing to do with Captain Man. He's doing it because he wants to cheer up Ray. This is the first time in the series, but probably one of the first time in Ray's life as well, that someone sees Ray as important outside of his powers or role as Captain Man.

I think this changed their dynamic, turning Henry (in Ray's mind) from a potential replacement, to someone he genuinely cares about and doesn't want to loose. I think this episode is what made Henry irreplaceable in Ray's mind and why Ray latched on to Henry as strongly as he did.

Stick with me there is one more episode I want to talk about before I talk about season 5 Ray.

Season 3 Hour of Power This was a big moment in the show. Henry finally has superpowers and was able to take down Drex, someone Captian Man couldn't defeat, by himself. This episode marks a huge dynamic change for Captain Man and Kid Danger. Because before Captain Man was very protective, and always took the lead on missions. Henry was starting to chaff at this, but it hadn't created any real conflict. Now, he has powers and has proven himself capable. So, Captain Man starts letting him take the lead.

Throughout the rest of season 3 and all of season 4 Henry is stepping up more and more, and Ray is taking a back seat more often than not. This is also the cockiest we see Henry throughout the series. He is ready to be his own hero proving himself more than capable.

All of this is almost exactly to plan, and this is where season 5 Ray comes in. Because Ray was pretty much ready to retire in season one, and as Kid Danger assumed more responsibility and started taking the lead on more missions, it set up the perfect opportunity for Captain Man to retire. He trained up a great hero, and a great replacement goal achieved.

Except, Ray wasn't ready to let go of Henry. Kid Danger was pretty much soloing most missions, so Ray didn't have the burden of superhero responsibility, and he had friends and people he cared about and who cared about him in turn. If he retired that jeopardized everything.

So, he effectively retired while still wearing the suit. The line between Captain Man and Ray blurred more and more, until it practically disappeared. Ray lost the sense of responsibility, because for the first time in his life, he wasn't burdened with being a superhero. Now Captain Man was just to hang out. He wanted to keep that forever.

I think that also explains his comment about not retiring for another 30-40 years in the finale, then retiring three years later. He was close to done in season one, but didn't want to lose Henry. When he lost Henry anyways, and was forced back into the responsibility of Captain Man, he was reminded of why he hired Henry in the first place. So as soon as Danger Force proved themselves capable he retired.

His behavior confused me for so long, until I went back and rewatched the earlier seasons. He goes from being someone isolated, lonely, and bearing a huge responsibility of protecting a city, unwillingly sacrificing everything outside of being it's protector, to (by season 5) having people who know and care about him, and as Henry becomes more capable, the crushing weight of being a superhero is alleviated, so the separation between Ray and Captain Man disappears.

Even at his worst behavior and his lowest points the worst consequences are his reputation. Until the finale, where both he and Henry have to contend with the fantasies they've built around themselves, and face both the issues and the consequences they've been ignoring.