1. Six Paths Sage: The Great Toad Sage, Gamamaru, was the first frog to master natural energy and taught his techniques to the Six Paths Sage. The Six Paths Sage became the first person to master frog-based ninjutsu and his Sage Mode is considered the most perfect.

2. Jiraiya: Jiraiya, one of the legendary Sannin, accidentally discovered Mount Myōboku and mastered Sage Mode under Fukasaku's guidance.

His Sage Mode had no time limit as he combined his power with the two Great Toad Sages.

3. Minato Namikaze: As Jiraiya's student, Minato likely learned his signature techniques. He activated Sage Mode during the Fourth Great Ninja War but was not particularly skilled at it due to his limited training time.

4. Naruto Uzumaki: Naruto's Sage Mode is often considered superior to Jiraiya's and Minato's because his appearance doesn't change significantly and he can activate it quickly.

However, Jiraiya's Sage Mode lasts longer due to merging with the two Great Toad Sages, while Naruto's duration is very short.

5. Boruto Uzumaki: The concept of inheritance is emphasized in Naruto, and Boruto is expected to learn Sage techniques to preserve the legacy of Mount Myōboku. While some believe Boruto should communicate with the Monkey King, Naruto convinces him to connect with the Toad Sages. Ultimately, any assistance in battle is valuable, whether it comes from frogs or monkeys.