Now the Manchester City star has his sights sets on fulfilling an even bigger wish as England get their quest for European Championship glory under way.
Grealish became a fan favourite as Gareth Southgate’s side made it to the Euros final at Wembley two years ago, only to suffer an agonising penalty shoot-out defeat under the arch. A trip to Euro 2020 final foes Italy lies in store as they kick-off qualification for the next edition tomorrow – England’s first match since their heart-breaking World Cup quarter-final loss to France.
Southgate’s squad scattered around the globe after that December defeat, with Grealish grasping the unique opportunity to visit New York around Christmas and see sights from Home Alone 2.
“I stayed in the (same) hotel,” the playmaker said. “You could get some mad room service, like 16 scoops of ice cream! Like what he got in the film. I’ve got an addictive kind of personality. The missus always says to me, even when I like a song, I just keep on playing it.
“I love that film, man. Someone had told me about it (the tour), so we went round Central Park. I’ve watched it so many times.”
As well as staying at the Plaza, Grealish visited sites from the film such as the ice rink and terrace in Central Park along with the giant Christmas tree at Rockefeller Center.
“I felt like a right little tourist,” he said. “I was in the back of the carriage thing and every now and again someone would say, ‘I swear that’s Jack Grealish’. I was saying, ‘mate, quick, speed up!’ I loved it.
“I love Christmas. My mum’s always made Christmas so special for me growing up, so I’ve always loved Christmas and I’ve always wanted to go to New York around Christmas time.
“Because of football we’ve never been able to. It was like a little bucket-list moment. I loved it.”
Grealish went to Dubai and New York with his girlfriend during a brief holiday following a World Cup that left him feeling like he “needed a little break”.
A shin issue that he suspects was down to running during the lockdown provided another reason to take it easy, making his appearance off the bench against Liverpool just a day after he returned to City a shock.
“I thought there was no chance I’d be involved,” he said of December’s 3-2 Carabao Cup win.
“Then in the f****** 70th minute he (City boss Pep Guardiola) tells me, ‘Jack, you’re going on’. I was like ‘f****** hell,’ because I was blowing out of my a***!”
Grealish was as surprised by that appearance as he was to hear he had already played 45 matches for club and country this season.
Back on the pitch the 27-year-old does not appear to fear burnout as he said “playing football matches is the best thing you can do”, especially as he is performing better than any time since his £100million move from Aston Villa in 2021.
“I feel I am in the best form, especially since I moved to City,” Grealish said. “I think it’s confidence. If you were to ask me one thing (that has helped improve his form), I probably would say confidence.
“At the moment, I just feel a bit like I did when I was at Aston Villa. I feel like one of the main players, and I feel that playing a lot, it is the fittest I have been, especially since I have been at Man City. That comes down to playing a lot of games on the bounce and playing in big games, just making an impact really.”
Grealish will have the chance to play in another big match on Thursday as England kick-off their Euro 2024 qualification campaign against reigning champions Italy in Naples.
The playmaker is “buzzing” that boss Southgate stayed on to lead the nation into another qualification campaign meaning Grealish could focus on ticking another item off his bucket list: to win a trophy with England. “The players are coming through and playing with so much confidence. I feel like the next one really could be our one. Everyone will be in their prime.
“I actually feel old at the moment but when I think about it, I will only be 28 at the Euros.
“It’s no secret that we all want to win a tournament – and I do think it is there to be done,” he said.