When Jeb Bush first entered the presidential race, exclamation points a-blazing, it seemed like the nomination was his for the taking. In April, The Hill laid out a confident plan for Bush's path to presidency, claiming that after New Hampshire, the rest of the states would be a cakewalk. Even by late October, The Huffington Post still thought he had a shot. On Saturday, Jeb Bush dropped out of the race.

By then, it was hardly surprising. He came in sixth in Iowa, fourth in New Hampshire, and fourth in South Carolina. But there was something deeper amiss. In recent weeks, Bush's campaign had taken on a new, darker kind of buzz — one where all eyes weren't on him to succeed, but to fail, and to fail in the most painful, awkward, embarrassing way possible.

There had always been something a little sad about how Bush didn't really seem to want to be running for president — "Iowan comforts sobbing Jeb Bush at town hall" is an Onion headline, but almost isn't. With a father and brother who'd been in the White House before him, Jeb was constantly on the defensive about his family while at the same time seeming like he had something to prove.

But Jeb was also hilarious. He was self-deprecating, dark, and found a kind of morbid humor in doing badly. Some of the best moments of the campaign have come out of his mouth.

And for that, we thank you Jeb. And hang in there, you joyful tortoise, you — you're finally free.

Here are Jeb Bush's saddest moments on the campaign trail, ranked:

21. Jeb Bush apologizes to his mom mid-debate for saying he smoked marijuana 40 years ago.

20. "Eat your heart out, Zuckerberg."

19. Whatever this meant.

18. Calling himself a "joyful tortoise."

17. Buy a new pair?

16. Okay.

15. Love ya:

14. Jeb! gets bulldozed by Trump...

13. ...And then mocked for it on SNL.

12. Jeb does technology.

11. The fact that this exists.

10. While suspending his campaign, Bush awkwardly makes an announcement: He's looking forward to going home to "sleep with the best friend I have and the love of my life."

9. Laughing on the outside, crying on the inside.

8. Jeb's turtles.

7. The number of retweets this has.

6. "I've got a lot of really cool things I could do other than sit around and be miserable listening to people demonize me."

5. That time Jeb Bush told a bunch of children that his dad sent him "into a deep, spiraling depression for days."

4. When Jeb confessed that the expectations were "so low."

3. :(

2. This extremely depressing moment.

1. "Please clap."