Probably 1999, The Corporate Champion was just too talented to be on a wrestling program, it was above every thing you ever saw in this industry in terms of cleverness, swagger, charisma, connection with the live audience, Rock made millions of fans, loyal forever during this run. Then his classic babyface run with the one minute promos on the turnbuckle every week with the reactions just getting bigger every week with him becoming the Top guy in the business in every category even with some horrible booking. Rock and Sock, the best chemistry ever for a tag team, record breaking chemistry. And along with all that, The Rock was by far the best and most consistent main event worker in the business, nobody put on more great matches than him that year, which was also the case for most of his career. The series with Mankind, with Austin, gave Taker and HHH their best matches that year etc.
2000 is close, nobody was bigger in and out of the industry than The Rock was in 2000, it was the biggest year ever for a wrestler in the history of the business, Rock broke every record and also transcended the industry like no other. From hosting SNL and drew record number for the season, to cut a promo at the Republican National Convention. Rock was so big, he got a RECORD BREAKING offer in the movie industry for his first role that year, a record that still stand today and just like 1999, he was putting classic matches and gave every opponent their best match of the year, from Benoit, to Angle to HHH. In 2000, Rock shattered every stigma that the media had on rasslin'. With all the positive in that massive year for him, there was also a negative for wrestling fans and that's the fact that Rock became bigger than the entire industry and his talent was too rare and versatile to be stuck in the borders of the wrestling business.
Besides 1999-2000, you can't just choose years for The Rock because he always evolved, like I said before, Rock 98 was a completely different character from Rock 97, Rock from 00 was completely different from Rock 99, Rock 03 was completely different from Rock 02 etc. That's what Rock does, he always changed his character, tone voice, promo style, ring work, it was always new and fresh. Same thing in his legendary 2011-2012 run, new promo style, ring work, character attitude, new and fresh, like The Rock always did in his entire career. The Rock thrives on it, on that rare connection he has with the fanbase, he's more aware to that aspect than anyone in history. The moment it's time to move on and evolve, he's doing it. He has too much pride in his work.
You can take a Rock match/promo from every year and see a big difference. Very few were as consistent as he was in the ring, wrestlers had some horrible main event matches. The Rock always delivered with every opponent which is why in every year he had the most or at worse Top 2 most great matches in the year in his full time career. 1998, 2001, 2001, 2002, 2003, 2011, 2012. All tremendous work in every aspect as a Top drawing act and an awesome main event worker. Created the most memorable matches and moments during that time and unlike any other guy in his position, used his superiority to make others, guys like Lesnar, Angle, Jericho, Foley, Hurricane etc. 2003 Hollywood Rock was exceptional and again, gave you a taste of why his talent deserved a much larger share of the world to really appreciate his greatness. The Rock is the greatest total package this industry has ever and will ever see. The GOAT.
In regards to 1999, the HalfTime Heat, besides the fact that it was a record breaking rating with the most wide audience for any wrestling match on cable TV at that time, with the most impressive thing that it was against the SuperBowl halftime show. It was also a comedic masterpiece, Rock's work during this match, from his reactions, to the one liners, to the improvisations on the spot not only verbally, but also with his antics, that was truly the peak of entertainment I have ever seen from the wrestling business, it was above brilliant and made casual fans, wrestling fans.
Watching The Rock's rise, knowing his background, and knowing now what he accomplished is one of the most inspiring stories I have ever seen and we should be grateful that we were able to witness such an amazing journey from the lowest of low to the Top of the world, and no one deserved it more than him based on his once in a lifetime talent alone. We saw a guy going from having $7 in his pocket, not only going on to become a huge Hollywood megastar, a worldwide brand, a pop culture icon, but to become the Maradona, Jordan, Jackson and Elvis of his industry and that's something I will never forget.