It has been voted one of the worst places to live in the UK twice, has one of the highest teenage pregnancy rates and was once dubbed the most obese city in the country.
But as Hull is just weeks away from taking up its 2017 Capital of Culture crown, US Ambassador Matthew Barzun has named it his most favourite UK city saying he uses the Venn diagram, which was invented in the city, up to five times a day.
Mathematician John Venn, who was born in Hull, East Yorkshire, in 1834, created flip-chart favourite the Venn diagram, which uses circles to represent sets and their relationships to each other
Mr Barzun says Mr Venn and anti-slavery campaigner William Wilberforce, also born in the city, are two of his heroes.
Having transformed its fortunes in the last decade, Hull is rejoicing after Mr Barzun said it will be the place he remembers "most fondly" when he returns home to Kentucky.
In his time heading the embassy in London's Grosvenor Square, Mr Barzun has made a point of travelling the length and breadth of the country, visiting 125 towns and cities in three and a half years.
But it was the fishing port that won his heart, rather than some of the big tourist sites that attract many more of his countrymen.
"If I had to pick one [place], Hull has particular resonance to me," he said.
"I had a wonderful visit in Hull. William Wilberforce and what he started here and what that did to change our country. John Venn, the great British mathematician who invented the Venn diagram, which I must use five times a day."
Mr Barzun said the attraction arose partly because Hull was the birthplace of two of his heroes.
He said Venn's famous diagram has regularly come to his aid when illustrating talks with a flip-chart and marker pen at some of the 160-plus schools he has visited across the UK as ambassador.
Matt Woodcock, a minister at Holy Trinity Church in Hull where Wilberforce was baptised, said: "It is wonderful to hear someone saying such positive things about Hull. It really is a phoenix rising from the flames story for Hull.
"I hope the ambassador can be our guest of honour when the Archbishop officially makes us a minster next year.
"Hull is the most underrated city in Europe and it’s great to hear him say this."
The same font used to baptise Wilberforce at the church is still used today.
This year Hull was named one of the top 10 UK destinations to visit by Rough Guides and is due to host the 2017 Turner Prize.
It has come along way from being given the dubious distinction of winning the inaugural Crap Towns: The 50 Worst Places to Live in the UK in 2003 to last year being named the second worst place to live in the uSwitch.com annual Quality of Life index.
Martin Green, CEO and Director Hull 2017, said: "We are thrilled that the US Ambassador is a fan of Hull and who can blame him? It's a wonderful city, with a great heritage, excellent cultural scene and a fiercely proud and independent population.
"It's also UK City of Culture 2017, meaning there will be many more reasons for the ambassador and his compatriots to come visit next year. They can expect a very big welcome."
The birthplace of poet Philip Larkin, Hull, which was the most bombed city in the country apart from London during the Second World War, is now home to The Deep, one of the UK’s biggest aquariums, and eight museums which have undergone multi-million pound investment.
Although having the utmost praise for Hull, Mr Barzun also said his favourite British treat is sticky toffee pudding.
It comes after he courted controversy after telling Tatler that he had had enough of lamb and potatoes after being served it "180 times" in his first year as Ambassador to the Court of St James.
"Sticky toffee pudding is something I'm going to have to learn how to cook, because I'm hooked," he added.
He said he had become a Liverpool fan, grown to love The Thick of It and his favourite sporting event has been kite-surfing, where he was one of 423 people who set a Guinness Book of World Records record for kite-surfing in June.