1. Incredibly successful and talented at what they do
It's hard to deny that Donald Trump is incredibly successful at...whatever his business is. Real estate? Casinos? Steak sales? I dunno - but whatever business he's in, it's clearly made him a lot of money - and in his SECOND chosen profession of politics, he's leading the Republican party after being at the top of nearly every poll for the better half of the last year.
And the same goes for Kanye West - his music is undeniably the work of an auteur who is deeply passionate and endlessly talented. He's one of the best-selling artists of our generation and has been given nearly every award someone in the music field could ever hope to get.
Both of these guys are talented and successful at their chosen professions. Regardless of your own personal opinion on either, you have to accept that.
2. Kind of hilariously boastful and self-involved
Sorry losers and haters, but my I.Q. is one of the highest -and you all know it! Please don't feel so stupid or insecure,it's not your fault-- Donald J. Trump (@realDonaldTrump) May 9, 2013
Both Trump and Kanye have made an art of being ridiculously over-the-top with their braggadocio and (possibly self-aware) arrogance. Trump constantly talking about how he wins everything how he's the greatest at everything, and bizarre statements about his high IQ and his total lack of racism. Kanye does much of the same - although West will sometimes let his guard down and admit to some flaws, only to eventually post a screenshot of a Google result for "Kanye West greatest".
Now they know pic.twitter.com/6c3OXYmkPG-- KANYE WEST (@kanyewest) February 9, 2016
3. Just....awful opinions, constantly.
Healthy young child goes to doctor, gets pumped with massive shot of many vaccines, doesn't feel good and changes - AUTISM. Many such cases!-- Donald J. Trump (@realDonaldTrump) March 28, 2014
BILL COSBY INNOCENT !!!!!!!!!!-- KANYE WEST (@kanyewest) February 9, 2016
C'mon, guys. Just....oof.
4. Constantly getting destroyed in Twitter battles
Note - the original tweets for both Donald Trump and Kanye West were since deleted, for EXTREMELY OBVIOUS REASONS.
Trump followed that perfect burn moment by flailing incomprehensibly about how much of a lightweight Danny Zuker is, EVEN THOUGH HE JUST HAD GOTTEN BURNED BY HIM AN INSTANT AGO.
And recently Kanye went on a long rant about Wiz Khalifa (and his wife/Kanye's ex, Amber Rose) after misinterpreting a tweet from Khalifa about "kk" (assuming he meant it as an insult to West's wife, Kim Kardashian, although Wiz meant it as "weed")
After 100% embarrassing Kanye to the max for ranting about an insult that didn't even happen, Amber Rose hopped in with this:
5. Anime is a key part of their appeal
Kanye is a pretty huge fan of anime and manga, and Donald Trump's support (apparently) comes from those who love anime.
For some reason, Kanye deleted this tweet about him watching Anime videos on Youtube at midnight the day before New Year's Eve. But thankfully he still expresses his love for Akira on occasion.
Anime - the uniting factor between Kanye West and Donald Trump!