WWE Monday Night RAW 25th anniversary: Ranking the 25 biggest stars

21. Ric Flair

I’m going to get yelled at a lot on this one but yes, you are reading that correct. Ric Flair is not in the top 20. While Ric Flair is easily on the Mount Rushmore of professional wrestling, his time on Monday Night RAW was obviously not the pinnacle of his career, even though he was around during the early days of the show.

After becoming one of the biggest stars in the world with NWA and WCW, Ric Flair jumped ship to WWE in late 1991 and quickly won the WWE Championship by winning the Royal Rumble for the vacant strap in 1992. Flair later lost the title but still competed at the Rumble the following year. He appeared in one of the biggest early matches in RAW history, losing a Loser Leaves Town Match to Mr. Perfect on Jan. 25, 1993, just the third episode in the show’s history. Flair had re-signed with WCW, and this was the last televised match of his first run in WWE.

After WWE acquired WCW in 2001, Flair returned to RAW as the co-owner of the company following the Invasion Angle and immediately got into a feud with Vince McMahon, which led to a Street Fight at the 2002 Royal Rumble pay-per-view. They would battle again a few months later for sole ownership of the company, with Flair losing after Brock Lesnar got involved.

Flair became relevant again in 2003 as he became the eldest member of Evolution with Triple H, Batista and a very young Randy Orton. He was a manager of sorts but eventually got back in the ring, even winning the World Tag Team Championship with Batista and later the Intercontinental Championship, a title he held for 155 days before dropping it to Shelton Benjamin.

Following the end of Evolution, Flair got into a decent feud with Edge, which resulted in a very solid TLC match on RAW in late 2005. After dropping the I-C strap, he got into a nice summer rivalry in 2006 with Mick Foley but things got a little strange after that. He won the World Tag Team Championship with Rowdy Roddy Piper, which just didn’t seem right at the time, and later teamed with Carlito, which would take him to the pre-show at WrestleMania 23, something you’d never think was possible. Ric Flair on a kickoff show?

The saving grace of all of that was his final run in WWE. After once again feuding with Vince McMahon, Flair was told that he would be forced to retire following his next loss. That did lead to some entertaining matches and moments on RAW for a few months, and the night after his loss to Shawn Michaels (his last match in WWE) at WrestleMania XXIV was one of the most dramatic nights in the history of Monday Night RAW as legend after legend appeared on the show to thank Ric Flair for his amazing contributions to the business.