At approximately 9:20 p.m. on Aug. 9, 1999, in a small suburb somewhere between downtown Chicago and O’Hare International Airport, a talented yet undervalued WCW wrestler stood with his back to 14,000 screaming fans. Arms outstretched and biceps flexed, Chris Jericho turned to face The Windy City faithful and the millions watching around the world, beginning what would become one of the most amazing careers in the history of WWE.

Almost instantly, Jericho went from cracking jokes with bumbling hap Ralphus to mixing it up with icons like The Rock and The Undertaker. Across the three decades that followed, Y2J became the first man to unify the WWE and WCW Championships, nearly blinded Shawn Michaels and faced off with Academy Award nominee Mickey Rourke, all en route to becoming a genuine pop culture sensation.

In a candid conversation with WWE.com, Jericho looked back at that legendary night in Chicago, the genesis of his catchy theme music, and what it was like to visit Mr. McMahon’s house.

VIDEO: Watch Chris Jericho's iconic debut on Raw, Aug. 9, 1999

WWE.COM: When did you decide you were going to make the jump to WWE from WCW?

CHRIS JERICHO: My goal was always to be in WWE. I could tell after about a year in WCW that WWE was still the place to go for a young guy. WCW was a place for older guys. If you came in at the bottom in WCW, you would stay there for the rest of your life. There was not a lot of room for upward advancement. I knew Don Callis, who worked with The Truth Commission in WWE as The Jackyl. He was friends with [WWE producer] Vince Russo, who was a big fan of mine. Don told Vince Russo that I had a year and a half left on my WCW contract and brokered a conversation between me and Vince Russo around Christmastime of ’97. Fast-forward to March of ’99 and my deal was up in June. Vince McMahon flew me to Connecticut to meet with him at his house.

WWE.COM: Is that the first time you met Mr. McMahon?

JERICHO: The first time I ever met Vince was in Calgary in 1997. They had the Canadian Stampede pay-per-view, which was so crazy. It was The Hart Foundation vs. Steve Austin’s gang. I was working for WCW at the time, but I said, “I’m gonna go to the show, I don’t care.” I was going into enemy territory, and one of my goals was to go say hi to Vince. I knew a couple people, but the Monday Night Wars were real, so that took a lot of [nerve] on my part. I just didn’t know any better.

WWE.COM: Were you anxious about going to the WWE Chairman’s house?

JERICHO: I was so nervous because I was a 28-year-old kid, and all I wanted to do was work for Vince McMahon. Shane McMahon answers the door, I go inside and at a table were Jim Ross, Vince Russo, [WWE producers] Ed Ferrara and Bruce Prichard, and Vince McMahon. They’re having a meeting … sitting there with the charts on the wall. This is secret stuff, dude. There was no real Internet, there’s a wrestling war, and here I am, a corporal on the other team’s army sitting in on this war meeting. I remember a couple times Vince even asking me, “What do you think about that, Chris?” And I was like, “Well, I think I like it. Sounds great to me!”

WWE.COM: Was there a moment when you were able chill out and not be so uptight that you were at Vince’s house? Were you able to relax?

JERICHO: Not really, no [laughs]. We went to Vince’s sunken living room, and there was this big giant oil painting of Vince on the wall. It might have been a painting of his whole family, but all I remember seeing was Vince.  I was just so freaked out probably blabbered on like an idiot saying things like, “If I came to WWE it would be the place for me to be, because WCW doesn’t give young guys a chance. If The Rock was in WCW he’d be in my position, and if I was in WWE, I’d be The Rock.” And Vince was just like, “Yes, OK, OK. Well, it was very nice meeting you, Chris. Keep in touch.” And that was the end of the meeting. I was expecting to have this like giant, million-dollar contract drafted up, but he just brought me there. I had no idea why. I asked him years later, “Why did you bring me there?” And Vince said, “I wanted to show you how much we wanted you here. I obviously couldn’t offer you a job because you still had a contract, but I wanted to see if I could trust you.”

WWE.COM: When were you finally offered a contract by WWE?

JERICHO: In June, Vince finally called me on the phone when my deal was up. It was the day Wayne Gretzky retired, and I put up a message on my answering machine saying, “This is Chris, I’m really depressed today and unless you’re Wayne Gretzky, I really don’t wanna talk to anybody. Leave a message.” Phone rings, guy on the phone goes, “Hello, Chris, this is not Wayne Gretzky, this is Vince McMahon. If you still feel like talking, please call me back.” I ran to the phone and Vince said, “We want you to come work for us and we’d love to have you.”

VIDEO: Watch Jericho's first return by breaking the code in 2007

WWE.COM: Were there any other in-person meetings before you debuted in Chicago?

JERICHO: Not really. I passed along the idea of the millennium countdown through Vince Russo, which Vince McMahon approved, and McMahon had the genius idea of having the countdown clock end right in the middle of The Rock’s promo, which I thought was just such a great twist. I did have one in-person meeting about a week beforehand where I went to Titan Towers to discuss my ring music and graphics.

WWE.COM: That music has become so iconic. When you heard that song, what was your reaction? You must have loved it since you’ve had it for so long, right?

JERICHO: When they first played “Break the Walls Down,” I didn’t know if I liked it because it wasn’t really what I was picturing. I listened to it a few more times and my one request was I wanted [WWE composer] Jim Johnston to add some heavier guitars to it, which he did. I think before that it was just a keyboard line. Once I was able to get those extra guitars, I really started feeling it. That’s why Jim’s a genius, because he always finds the right attitude for what the performer does. He really tapped into the attitude of Y2J before I even knew what that was. A bit of swagger, a coolness, arrogance and confidence, but in a real swanky, cool type of way. There have been a couple times when I’ve wanted to change it, but Vince always said, “No, you’re theme is evergreen. It’s never gonna change. As long as you wrestle here, that will be your theme song.” And he’s right. Vince is always right. It is an iconic song and it is the perfect song for me to come to the ring to.

WWE.COM: Was there ever a discussion of changing your name or were you always going to be Chris Jericho?

JERICHO: Always gonna be Chris Jericho. I had trademarked that name. The first match I ever had in Ponoka, Alberta, Canada, on Oct. 2, 1990 — my name was Chris Jericho. I got a trademark on it in Minneapolis when I was getting ready to leave WCW.

WWE.COM: Getting back to the millennium countdown, what was the genesis of that idea?

JERICHO: I was in line at the post office and there was a countdown clock to the new millennium on the wall. I remember thinking, “That would be a great way for somebody to come into WWE … wait a second, that’d be a great way for me to come into WWE!” The idea was to be the millennium man coming to save WWE, and a whole new era was arriving. That’s what we were all going through in 1999. There was a lot of uncertainty about the year 2000, from both a biblical and technological standpoint. There was this thing called Y2K, which was a computer bug that apparently could crash the entire world. Airplanes could fall from the sky and all this stuff, because when computers were invented, the clocks only went up to 1999, and when 2000 hit, it might screw up the entire time-space continuum or whatever they were saying. So I wanted to call my finishing move The Y2J. When I told Vince, he said, “No, Y2J is your name. We’ll come up with something else for your finishing move, but Y2J is your WWE name.” He let me keep Chris Jericho only because my nickname was going be Y2J, like Triple H or HBK. I needed it, because it was a whole new era for me. Having the Y2J name made a big difference in establishing a whole new persona.

WWE.COM: How long after that did the Lion Tamer become the Walls of Jericho?

JERICHO: Fairly quickly. At that time, I had the Lionsault and the Lion Tamer. Vince said we couldn’t call it the Lion Tamer because Ken Shamrock was using the Lion’s Den [structure]. The Lion’s Den was only there for that one week. That’s it. Had it been the week before or the week after, the move would still be called the Lion Tamer to this day. There were these ideas for finishers for me and the names on this list were just terrible. There was The Salad Shooter, Rock n’ Roll Finisher, Ego Bruiser was another — just these really bad names. Then I just said, “What about the Walls of Jericho?”

WWE.COM: How did the actual night of your debut go in Chicago? Was it one of those scenarios where you were flown in to a different airport to keep you hidden?

JERICHO: No, that didn’t happen until 2012 and 2013. They flew me to Detroit, because that’s where Sunday Night Heat was. In those days, they did Sunday Night Heat live. I sat next to Vince to get a sense of how things worked.

VIDEO: Watch Jericho's silent return in 2012 during "the end of the world as you know it"

WWE.COM: Did you think that big things were in store for you, since you were interrupting one of WWE’s biggest stars, The Rock, that night?

JERICHO: I wasn’t told that, but I knew what was up. I knew Vince had to go through some hoops to get me. The fact he brought me to his house, dude, I mean c’mon, right? The contract I got was a huge contract at the time, although it was half of what WCW ended up offering me to stay. I didn’t care. I did not want to be there. I wanted to escape. Guys knew what I was making, so there was a big target on my back when I walked in the door. I came in by myself with no real friends, no one I could really trust, and no one telling me how to do things. I was the brash, outspoken Jericho, and I got a lot of heat right off the bat.

WWE.COM: How did being in Chicago affect the reaction from the crowd that night?

JERICHO: I think 50 percent of the people had a feeling it was gonna be me. I wasn’t a big star, but I had a cult following from WCW and Chicago was always a big building for me. I did  the famous “Man of 1,004 Holds” promo in Chicago, so there were a lot of Jericho signs and a lot of anticipation. When the countdown ended in the middle of Rock’s segment, and “JERICHO” appeared in giant letters on the Tron, people went nuts. It was probably my biggest reaction ever, with the exception of Phoenix at Royal Rumble 2013, although this year in Memphis [on Raw] was pretty good too. Chicago is always loud; it’s the ultimate place to go. Now, it would have been a great entrance anywhere, but it definitely didn’t hurt that it took place in Chicago. It added a lot to the overall legendary status of it. But I went a little too long, and some of my facial expressions were very cartoonish. Even though it’s a classic, It’s still a little bit cringe-worthy for me.

VIDEO: Watch Jericho's stunning return as entrant No. 2 in the 2013 Royal Rumble Match

WWE.COM: What was it like when you walked backstage afterward?

JERICHO: I don’t remember anyone saying anything. It was just a business as usual type of vibe, because for those guys, it was just another night. I knew I had to hit a homerun that night, but I thought it was more of an inside-the-park homerun than an over-the-fences homerun. I remember Vince saying, “I’m gonna be watching you like a hawk, and anything you do wrong, I’m gonna tell you.” A few weeks later, he wasn’t really on me like a hawk. I went from the palace of the kings and queens to the gutter eating pork and beans, from the penthouse to the outhouse.

WWE.COM: Why was that?

JERICHO: The night after I debuted, I did the same thing I had done to The Rock to The Undertaker. Not knowing any better, and kind of forgetting there was a hierarchy, I did this whole thing about how boring The Undertaker was, and how he wasn’t the personification of evil, but the “personification of boredom.” The big problem was he had just done this long, 20-minute promo. Talk about bad timing. It just put a nail in my coffin.

VIDEO: Watch The Undertaker respond to Jericho's controversial interruption

WWE.COM: How long after that debut in Chicago did you feel settled in as a bona fide main eventer?

JERICHO: To be quite honest with you, not until I became the suit-wearing, slow-talking Chris Jericho with the Shawn Michaels rivalry in 2008. That was the first time I lived up to all the potential that I had over the years, and really understood and embraced what I needed to do to be a legitimate top guy. When I was the Undisputed Champion [in 2001 and 2002], I wasn’t in a top guy position. At Live Events, I’d be in the last match before intermission, but Steve Austin or The Rock would still be in the main event. I did a lot of great stuff in the first few years I was there, but it wasn’t tippy-top level stuff. I flirted with the main event a few times, but it wasn’t until 2008 that everything clicked.

VIDEO: Watch Jericho vs. HBK in a classic Ladder Match for the World Heavyweight Title | Full pay-per-view available on WWE Network

WWE.COM: Does the ’99 debut in Chicago remain your favorite entrance?

JERICHO: I don’t wanna downplay this year in Memphis on Raw either, because that was a great moment, but I think my all-time favorite is probably January 2013 at the Royal Rumble in Phoenix, because it was a legitimate shock that nobody saw coming. I think the reaction was maybe bigger than Chicago. But it’s “The Godfather” and “The Godfather Part II.” Both are amazing. I think 2013 might be a smidge better than 1999 only because it showed real longevity that I could still be contributing at the level I did 14 years earlier. It was a great reestablishment that Jericho was back and still here to kick some ass.

VIDEO: Watch Jericho's most recent comeback that's ruined by Bray Wyatt