This Is the Car James May Regrets Selling the Most

Image Credit: James May's Planet Gin

Automotive legend, former Top Gear and The Grand Tour host, and now gin connoisseur James May recently sat down for his YouTube channel to answer a few questions posed to him by viewers. This included one that asked him which of his cars he regrets selling the most.

May has owned some great cars over the years, and recent additions include the Triumph Stag he used in the final The Grand Tour special with Jeremy Clarkson and Richard Hammond. But all of us have cars we have owned that we really regret selling.

This was just one of the questions that May was asked. Being open to the viewers, there were some slightly unusual ones pitched to May, including asking if he would ever straighten his hair, much like that of Lucy Brown, who helps run his channel and create the videos.

But of course, the real reason we are here is to find out what car it is that May regrets selling the most. We can imagine viewers were racking their brains to try and remember what May has owned, and to see if they could guess which car he really misses.

Which Car Does James May Miss the Most?

 

“I don’t generally regret selling cars,” said May in his video. “Because I sell them for a reason,” he added. He did admit, however, that he feels he was a bit foolish to sell his white Porsche 911, specifically a 997 Gen II C2S model of the 911. That is one car that stands out for May, and for a good reason.

Discussing why he felt foolish, May said, “Because even though I got a good price for it, it really hadn’t depreciated that badly over 15 years, and I sort of feel it was an excellent example of a sort of basic 911.” May said it felt like a great analogue Porsche 911, and it drove great, so it’s certainly a car he wonders if he should have ever sold on. But May did buy another 911 and didn’t think he should have two in his collection, hence the sale of his white one.

Hilariously, Lucy Brown has clearly dug through the archives to find a clip of May discussing the car. In this clip, he said, “Never sell your 911; you’ll always regret it.” In the present, however, May said, “Maybe that was a mistake, but I am sure I will get over it.” So, while he doesn’t tend to have regrets about the sale of his cars, May does wonder if that particular one was one he should have kept in his garage.

What Else Did May Discuss in the Q&A?

James May reveals the car he regrets selling the most selling Kawasaki
Image Credit: James May’s Planet Gin

There were a few other interesting questions posed to the motoring legend during the video. One of them asked which car he was going to sell next. While May said he wasn’t selling a car, he did say he was selling a motorcycle. Specifically, he’s selling a “Kawasaki Z900 Cafe if you are interested. “It’s in mint condition, it’s done under 2,000 miles, and it is in Kawasaki bright green, a lovely bike,” said May. He is just selling it to free up some space and because he doesn’t use it enough.

May was asked about the new electric Jaguar that is on the way. He said, “It is supposed to be different thinking, but it’s styled like a limousine from the ’30s with a really long bonnet, as if there is a V12 or a straight-eight under it. “And that is the one thing it doesn’t have because it is electric,” added May. Those are just some of the questions that May answered, which he did so in his usual entertaining, thoughtful, interesting, and hilarious way.

Author: Henry Kelsall

Henry joined Guessing Headlights in May 2026, and covers a wide array of topics ranging from EVs, American barn finds and supercars.  He’s combined his passion for cars with an interest in motorsports and steam locomotives, and has been an automotive journalist for over ten years. Henry has written for various publications including HotCars, AutoEvolution and most recently as a content writer for Supercar Blondie at SB Media.

Henry’s main love is for anything Japanese, or from Lancia, with the dream being to one day own a first-generation Honda NSX. Away from work, he partakes in his passion for steam engines, and is currently a trainee fireman at a British heritage railway.

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