#1. WWE legend The Rock and current Universal Champion Roman Reigns
The Rock won the Royal Rumble match back in 2000, but this wasn't actually the WWE legend's first Rumble match. The Rock entered his first Royal Rumble back in 1998 where he entered at number four and lasted for 51 minutes before being eliminated by Steve Austin.
The Royal Rumble in 2000 saw The Rock enter at number 24 and last 14 minutes before winning the match and going on to WrestleMania. The Rock has left quite the legacy in WWE and it appears that the mantel has been picked up by his cousin, Roman Reigns, who has been part of several Rumble matches himself.
Reigns' first Rumble came back in 2014, where he was the runner-up to Batista before winning the match itself in 2015. The following year, The Tribal Chief was forced to defend his World Championship inside the match but it was Triple H who came out victorious.
Roman Reigns was the number 30 entrant in 2017, the 28th entrant in 2018, and he even entered at the 26th position in 2020. But The Tribal Chief hasn't been able to recreate his magic from 2015 in recent years. Reigns came close in 2020 when he was the runner-up to the eventual winner, Drew McIntyre.