(1: 2000: Fiat Multipla

The Fiat Multipla is unspeakably a disaster. The unnecessary headlights under the windshield and weird minivan-like shape are atrocious. Who would buy this?
(2: 2001: Pontiac Aztek

One of the only things that the
Aztek is known for is its ugliness. The double headlights and puffy bumpers just make it worse.
(3: 2002: Plymouth Prowler

The Prowler is unique, but maybe a bit too unique. It does not resemble any other car on the road today. Wait... is this even a car?
(4: 2003: Buick Rendezvous

The Buick Rendezvous is the ugliest crossover ever made. The huge taillights and strange rear window are what makes it so revolting.
(5: 2004: Chevrolet SSR

The Chevrolet SSR performance pickup didn't last long, and that's because it doesn't look like a Chevy, or a pickup. It looks more like it wants to be a Camaro.
(6: 2005: Chevrolet HHR

The Chevy HHR came out to chase Chrysler's just-as-ugly PT Cruiser. They even hired the same designer. But, the result was just as bad as the SSR.
(7: 2006: Chrysler Aspen

Nowadays, we are begging Chrysler to introduce a Durango-inspired SUV to the market, and that's just what they did back in 2006, and it wasn't the best. Maybe that's why the brand is sticking to minivans...
(8: 2007: Jeep Compass

The current Jeep Compass was a breath of fresh air when it debuted in 2018. Why? This. The first Compass crossover came out when Jeeps (except the Wrangler and Liberty) were failures.
(9: 2008: Dodge Nitro

Before the now-discontinued Journey, Dodge had another outdated crossover: the Nitro. The fenders
(10: 2009: Nissan Cube

The Nissan Cube was introduced to the US market for a short period of time. It is one of the ugliest cars in history, and you can see why.
(11: 2010: Honda Element

The Honda Element competed with three other ugly crossovers on this list: Kia Soul, Nissan Cube, Jeep Compass. ust like the others, it failed miserably.
(12: 2011: Nissan Juke

The Nissan Juke is known as one of Nissan's most revolutionary designs, but it doesn't mean it's pretty. Nissan discontinued it in the US not that long ago, while foreign markets enjoy a redesigned version.
(13: 2012: Kia Soul

The Kia Soul's more mature second generation arrived last year, leaving behind the unique first generation. It sold rather well, which is why it remains in the lineup.
(14: 2013: Aston Martin Cygnet

The Cygnet was an embarrassing situation. Oh, and yes. Aston Martin, the creator of the luxurious DBS and speedy Vantage, made this. We're not kidding. The iconic Aston design cues look far too big for the ultra-tiny city car.
(15: 2014: Honda Crosstour

The Honda Crosstour is a quirky sedan-like coupe-like crossover-like wagon-like vehicle that barely sold at all, leading to its demise.
(16: 2015: BMW i3

The beautiful BMW i8 and strange i3 were introduced together in 2015, but of all things, the i8 was discontinued instead of the i3, and BMW has no plans to drop it.
(17: 2016: Toyota Prius

The iconic Toyota Prius hybrid was never a good-looking car, and in 2016, it got worse than ever. Those taillights... Thankfully, the Prius was toned down for the 2019 model year.
(18: 2017: Honda Clarity

The Honda Clarity was introduced in 2017 as an alternative-fuel vehicle, offering EV, PHEV, and HCV options. The EV was dropped recently due to incredibly slow sales. Could the PHEV and HCV follow?
(19: 2018: Chevrolet Bolt EV

GM is going all in on EVs, with the 2018 Bolt hatchback being their starting point. Currently, it is not the best-looking car in the world, but it is being overhauled soon.
(20: 2019: Toyota Mirai

The Mirai is the ugliest car we've ever seen. Ugly? Revolting? Alien-like? There's no word to explain how ugly it is. But, not to worry; theres a beautiful redesign arriving in 2021.
(21: 2020: Chevrolet Silverado HD

The fifth Chevy on this list so far is the Silverado HD pickup. The thin headlights and big grille are too much.
Finalists
2011 Mazda CX-7

2019 Mitsubishi Eclipse Cross

2020 Chevrolet Camaro SS

2007 Chrysler PT Cruiser

2020 Chrysler Voyager

2021 Toyota Sienna

What a fantastic post! Some of these models, along with your commentary, made me laugh.