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."

I met a fellow joyful tortoise on my way to the Reagan Library http://t.co/2355xaxdXO pic.twitter.com/ZXzMvQJKfB — Jeb Bush (@JebBush) August 11, 2015

17. Buy a new pair?

Jeb Bush sports black shoes held together by scotch tape https://t.co/tdi0hau53Q pic.twitter.com/sIYQWnBIJQ — NewYorkBestOf (@NewYorkBestOf) February 8, 2016

16. Okay.

Jeb on debates: “I’m not really disciplined, my mind wanders” — Zeke Miller (@ZekeJMiller) February 10, 2016

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.

Bush gave Zacharie, 13, a tiny turtle & told him "slow and steady wins the race." Bush carries them in his pocket. pic.twitter.com/wCmaKeDiKS — Ashley Killough (@KilloughCNN) January 6, 2016

7. The number of retweets this has.

Happy Birthday, Governor @JebBush from your friends at @FloridaHouseDC! Retweet to wish him a very happy birthday! pic.twitter.com/GA6bDn8nKJ — Florida House (@FloridaHouseDC) February 11, 2015

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."

Jeb on George HW: "All he would have to say is 'I'm disappointed in you' and it would send me into a deep spiraling depression for days" — Benjy Sarlin (@BenjySarlin) November 4, 2015

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

— John Whitehouse (@existentialfish) January 29, 2016

3. :(

To-do list from the Iowa field office: pic.twitter.com/xViJLYvSMe — Jeb Bush (@JebBush) November 9, 2015

2. This extremely depressing moment.

This is easily the most heartwarming Jeb Bush gif in existence. pic.twitter.com/LzqYGkTTLC — CAFE (@cafedotcom) February 4, 2016

1. "Please clap."