He's a Bathurst winner and Barry Sheene Medalist, but it wasn't always smooth sailing.
Time as a Walkinshaw junior led to an initial break but fizzled out, while there was a messy divorce from his second home, Kelly Racing, after time on the sidelines.
Success came in a factory Ford, before Reynolds was squeezed out, ultimately landing at Erebus in 2016 to lead its rise up pitlane.
Ahead of his milestone race on Saturday night, Supercars.com reminisced with the now-33-year-old.
Reynolds could have debuted with the HSV Dealer Team
Race 1 was back in 2007, with PWR Racing alongside Cameron McConville at the Sandown 500. You were within the Walkinshaw Racing fold at the time, what do you remember about how it came together?
I was part of [Walkinshaw’s] young-driver program, it was almost like the Holden Young Lions that they wanted to revamp.
I was in line to drive one of the HSV Dealer Team cars with either [Garth] Tander or Rick Kelly, and they were one-two in the championship at the time.
But I was fully green, full rookie. I didn't want to have that pressure on me, to have a big say or a big stuff-up in their championships.
They moved me aside to PWR and I got the drive with McConville, who was a very good teacher.
He was very experienced, the cars weren't the best but he was a lot of fun to deal with and very professional.
It's probably worth noting you weren't even in Super2 at this stage...
I was in Carrera Cup, trying to win the championship in 2007.
It was just a really big ask for someone as inexperienced as I was to do the job. I kind of didn't want to do it.
I was going up against some very good co-drivers in very good cars and I put my hand up and said 'I'm kind of out of my depth here' and I'm kind of glad I did.
It could have gone really good for me and made me look like a superhero or it could have gone really bad and I could have messed it up and ruined the start of my career.
It all sort of happened really quick. I think I had the meeting and I said 'listen, I'm kind of out of my depth' and they took it onboard.
And very quickly [Paul] Radisich kind of came up as a potential option (after splitting with Team Kiwi) and a very, very good driver.
Even if I didn't say that, they might've got him anyway. It all happened quite quickly.
Tell me about that Sandown weekend itself.
I remember driving out of pitlane for my first session and it was sort of half-wet, half-dry. I was like 'what have I got myself into? What is this car?' I had no idea how to drive it.
Back then, the cars were very difficult to drive, unlike today where all the young kids can come in and drive the cars quite on the money.
I couldn't believe what I got myself into. I felt like I was miles off the pace.
I can't even remember how the race went, I know we didn't finish. I think someone drilled me and it stoved in the rear three-quarter and they couldn't fill it up or something.
It was just very, very different back then. How the cars were, how the teams operated.
It seems like everything's a lot more refined now, the cars especially, because everyone's got more or less the same stuff in the cars; Car of the Future brought everything in line.
I kind of wish I did take that HSV Dealer Team drive, just to see what happened.
I took a different approach and I have no idea what would've happened if I took the drive in a good car.
I would've had good support, probably could've fast-tracked my career, maybe made me look a lot better than I was, who knows.
Then you headed off to Bathurst and didn't actually start the race.
It expired on the warm-up lap. Warming it up in pitlane it wasn't sounding that good.
Leaving pitlane, Cam said it was sounding terrible, he made it to the grid but it was making terrible noises, wasn't running well.
Then he went out for the sighting lap to take the green flag and it expired at Turn 2. In hindsight, the car wasn't that good to drive.
I remember driving out of pitlane for my first time at Bathurst in that car and I nearly binned it at Turn 4.
I was so close to binning it, it scared the pants off me, and it took me ages to get my confidence back again.
That was just my outlap, it wasn't the beat thing to drive. I think when you're racing, you've always got to be in the best equipment.
For Race 50, we fast-forward to Townsville in the middle of 2011, with Kelly Racing and your second full-time season.
I made the Shootout that weekend. I think I qualified third and that third prompted Tim Edwards to call me the week after to find out if I could move across to Ford Performance Racing, and The Bottle-O Racing car for 2012.
Lap of the Gods, Reynolds edition.
I know. That was interesting times. That's when you could run the soft and the hard tyre [in the same weekend] and I think we opted for the soft tyre straight away.
I remember my coolsuit failed on the grid and I was cactus, about 20 laps in I was overheated. It wasn't very good for me, that day. I remember it was quite hot.
I think I crashed with [James] Courtney trying to get myself into pitlane, he wasn't too impressed with me, because I had an electrical failure as well. The car was sort of shutting down, that's why the coolsuit switched off.
But my car was quite good to drive. I remember with my engineer James Small, we made it quite good to drive.
He was a good engineer, he taught me a lot, and now he’s killing it over in NASCAR [with Joe Gibbs Racing].
And he still watches our races, he texts me if I've done well or done shit he'll bag me out.
That 2011 was your return to the main game. You had a single year with Walkinshaw Racing in 2009, but were then relegated to the enduros and a bit of Super2 the following year. How did the Kelly drive come about?
I think I did quite a good job in the enduros with Will Davison [at HRT]. And I was co-driver with Fabian [Coulthard] in the Bundaberg Red car at the Gold Coast race. They signed me after that, I was a full-time driver again.
It was a lot of fun, until towards the end of the season when I wanted to change teams. I was a young kid full of ambition and the FPR cars were very good.
I had an opportunity to drive for a better team and as a driver, if you can't see a future with the current team you're with, what's the point in staying.
Reynolds with James Small
How tough was that situation to navigate?
It kind of got very messy. I wasn't allowed to go to the workshop, into debriefs and stuff like that. It got very, very messy.
After the Phillip Island 500, they sacked Smally, walked him out. It was quite a bad situation for myself to be in.
But I always had the thought I was going to a better place in Ford Performance Racing.
There was a lot of legal stuff that happened between then and the start of the next season. Mentally, it was quite hard for me to deal with.
You ended up joining FPR in 2012, what do you remember about that first season?
I had a lot of front-row starts in 2012 but never really made one stick.
I think Phillip Island 2012, I was leading, I had a couple-of-second lead to [Mark] Winterbottom and I think it was a shorter race back then, and I came in to get some fuel and the fuel-hose split so they couldn't get the fuel in.
That possibly could have been my first race win, four or five events in.
Phillip Island, 2012
You arrived at a good time in 2012, the cars were very quick out of the blocks.
There were a lot of things they did over the summer break and even during the year they added things in, like the water brakes, front and rear.
That was a big, big help to car performance. We used to carry around like 35 litres of water just to spray on the brakes and the rims and we had all these different settings on the dash.
It was really cool, you had your water-trim settings and fuel settings as well.
You were constantly trying to fix your car performance or balance by how much water you put on either end of the car. It was a lot of fun, but it was all banned after that.
Your second season with FPR was 2013, the year the Car of the Future came in. And you brought up your century with Race 100 early on, at Pukekohe.
It was an OK year. Very up-and-down year for I think the whole category because with a new car everyone was sort of coming to grips with how to drive them and the set-up windows.
We had a test day at the start of year, and my engineer was James Small and between the test day and the first race meeting we lost two degrees of rear wing, which completely killed our set-up, completely killed our car, it was terrible to drive after that.
My engineer got swapped from Smally to Nathaniel Osborne. James went to Winterbottom's car and I got Ozzy.
I wasn't too happy with it because the only reason I went to that team at the start was to have James there with me.
Reynolds claimed his first win on the Gold Coast in 2013, with Dean Canto
You did still get your first win that year, before 2014 brought your next milestone race, your 150th in Townsville.
'14 was quite a bad year for us, results-wise. I don't think we got many results at all.
I can't remember too much about it, but at the end of that year they sat me down and said 'you have to perform or we're going to sack you'.
Every now and then we went OK. I think we got a podium right at the end of the year, Homebush.
We changed our set-up quite dramatically for that round. It transformed the car and made it driveable. I went from nowhere to something, so that was a good day.
What we learnt at that race we took onto the next year. Obviously the bodyshape changed and the FG X came along and it was a much better car than the FG.
Winning at Hidden Valley, 2015
2015 did end up being your last year with FPR, or PRA as it had become, but not because of a lack of results. It was a genuine step forward with the FG X.
I don't think the FG was the best car to drive, the FG X had much more grip. It was just better everywhere.
I had the FG in the pre-season test and in the first round and I went nowhere. I think I qualified half-OK in Adelaide but in the race it was terrible, the tyres were going off and I got crashed into.
I think [Michael] Caruso crashed into me actually. I had a big train of cars behind me, a huge train, and I think he tried to pass the car behind me and stuffed it up and hit me!
But in the next round I went into the FG X and I went from mid-pack to the front of the grid.
All of the changes were the bodyshape. Nothing else changed. It was literally one week later. And everyone's like 'oh, Reynolds, you've remembered how to drive!' and I'm like 'oh, yeah, piss off'.
Phillip Island, 2015
By the time we got to your 200th race at Phillip Island in November 2015, you were in the strange situation of being a title contender but also being on the way out of the team. How did that unfold?
My intention was to stay the whole time. I had a few other deals come and go because I was still hanging onto something that possibly wasn't there.
It was quite a hard time because my lawyer, who's also my mate, Sven Burchartz, bought into the team in 2014.
I'd known him for 10 years or something and he helped me a lot through my life. He was almost my pseudo manager at times.
He bought into the team and he was always trying keep me sane, saying 'we're working on something'. But nothing really came about.
At the Gold Coast race in 2015, I signed the deal with Erebus in the hotel room of Betty's. It's all in the past now.
You won races, took a bunch of podiums and finished third in the championship. Was it weird to be having a breakout year but also lose your seat there?
It was quite weird. At the end of '14 they said 'you have to perform or you're going to get sacked'.
I finished third in the championship, did my job, helped Mark and the team win the title. And there was nothing there at the end.
It was an odd situation probably for both sides. They lost Pepsi Max as a sponsor and Bottle-O was a very big sponsor, Winterbottom took that sponsor I suppose and they had nothing left for me.
It was probably an awkward time for both parties. I wanted to stay but there was no real chance of me staying.
Was there a moment you knew the door was closed on staying?
Probably after all of the 'p-wagon' saga (at Bathurst, where Reynolds was fined for a press-conference comment).
After that all happened, the communication wasn't the best, but it kind of stopped.
I don't think that had anything to do with the outcome, the timing of it just made it look worse.
They were supposed to have an answer [on a 2016 drive] the week before Bathurst, then the week of and I heard nothing so I just assumed the worst and moved on.
It's all in the past now. Joining Erebus has been the best thing I've ever done, not only for my career but my mental health, everything.
My whole life's just improved out of sight.
Reynolds' Erebus debut, Adelaide in 2016
The Erebus you signed for was a Gold Coast-based Mercedes squad, but ended up in Melbourne running Commodores in 2016. That was quite a shift, but it's worked out well.
Exactly. It was a very good outcome. I always try to make the best of any situation given to me.
There was a very different landscape to the one I originally signed the deal for and what I ended up racing in 2016.
I was actually looking forward to getting out of Melbourne and going to live on the Gold Coast and doing that sort of stuff, but over the summer break they basically restarted a brand-new team in Moorabbin in Melbourne.
They hired all new staff, the only two people who came across were Barry Ryan and Campbell Little.
The cars turned up [from Walkinshaw Racing] two weeks before the first round, it was quite scrappy at the start. It was scrappy for a while.
The team was quite green, a lot of the people hadn't been part of Supercars before, so pitstops were a drama.
Barry was teaching everyone how to go racing from scratch. And if he had his time again, I don't know if he'd do that because it probably sent him a bit crazy!
We've still got some of the same people there today and that's the beauty of our team. If you're a misfit or unwanted from a team, generally we can make the most of you.
One of those misfit recruits was Alistair McVean from Clayton just before Bathurst 2016, which ended up being a key addition.
The best person we've employed was probably Al. He was just so, so good, brought a lot of structure, a lot of intelligence and a lot of wisdom that we needed so badly.
He was brilliant, and he's still probably the best person I worked with in the sport.
McVean in the Erebus garage at Sydney Motorsport Park in 2017
Your 250th race came at Sydney Motorsport Park in August 2017, your second season with Erebus. A couple of months later you were a Bathurst winner...
That's the best achievement we've had as a team and I think the proudest achievement I've ever had in my life.
To start with a team that was like that in 2016 and to end up where we are now, and even where we ended up in 2017, was just an unbelievable story.
As soon as Al joined, and the car from Bathurst '16 to Bathurst '17, we evolved so much and made new parts basically every race meeting to try.
The evolution of the car was incredible, every time we rolled out at a different racetrack, the car had different parts in it.
I love that about our sport, you can always solve problems by engineering it better.
Reynolds won Bathurst with Luke Youlden in 2017
And it's still trucking along with a good upwards trajectory as we approach your 300th race this weekend.
I'm really looking forward to this race. We probably should've won there last year if [Scott] McLaughlin didn't get such a good run through on the Sunday.
That was probably our race we could've won. We ended up second, which is cool, but winning's always better.
I nearly threw it away on the last corner, that was me being a dickhead, it was a lesson that you need to focus all the way to the chequered flag.