While he made his debut in 1999 and came off the bench twice at EURO 2000, Heskey's England career well and truly sparked into life a year later.
On a rainy night in Munich in September of 2001, the then-Liverpool man scored to put the finishing touches on a famous 5-1 win over Germany in a World Cup qualifier that he told Flashscore was the best match of his career.
Establishing his importance to Sven-Goran Eriksson's side, it ensured that he would fulfil one of his biggest dreams a year later, with the striker chosen as one of 23 players to head to South Korea and Japan to represent England at the 2002 World Cup.
"Right up there," Leicester-born Heskey says when asked where playing at the World Cup ranked among his career highlights.
"As a kid, you always - they're the memories you have, watching the World Cup. I was watching John Barnes, Gary Lineker's from Leicester so watching him score loads of goals. And then you dream to play in one."
While he got to live that dream at the age of 24 though, he quickly found that it came with some difficulties.
"It's not easy," he says.
"You're getting on with each other, and you've got to remember that a lot of us have grown up together - I obviously knew Michael (Owen), and I played at Liverpool at the time, so I knew a few Liverpool players - but... It's an interesting one, because you're in a foreign country but you don't get to see the foreign country. You just see your hotel rooms and different rooms within the hotel.
"Boredom is a tough one," he continues. "Especially for players who don't like their own company, and there were quite a few of them."
However, Heskey and the England squad were able to get out and about a little during the 2002 tournament, thanks to the celebrity status of one of his teammates.
"We were lucky, we had David Beckham. He would shut down a mall, and then we'd go and just walk around the mall, mainly just to get out of the hotel."
On the pitch in Asia, England finished second in their group thanks to a 1-0 win over Argentina, and Heskey then scored his first World Cup goal in their 3-0 win over Denmark in the round of 16, but a star-studded Brazil side claimed a narrow 2-1 victory to knock them out.
It's a defeat that still stings for Heskey, who felt he and his teammates could've done something special that summer.
"If it wasn't for Ronaldo, Rivaldo and Ronaldinho, we would've probably had a really good chance of winning that...
"It was (painful), and for me personally, I wasn't ready to go home. I was ready to go further.
The striker remained an important part of the England setup after that, but fell out of favour after EURO 2004, not being called up for over three years. During that time though, he never doubted that he'd represent his nation again.
"I knew I was going to play again," he remembers. "I knew what I could give and what I could bring. It was only a matter of time."
He was proven right, thanks in large part to Owen. The two had forged a close connection during their time as strike partners for both Liverpool and their country, and the 2001 Ballon d'Or winner convinced England manager Steve McClaren to bring Heskey back into the fold in 2007.
"It was Michael. Michael had a word. He said, 'Bring him back in,' and yeah, I came back in then, and then stayed in."
England missed out on EURO 2008, failing to qualify, and that led to the appointment of esteemed manager Fabio Capello, who was tasked with taking them to the 2010 World Cup.
Capello took a liking to Heskey, who became his first choice for the spot next to Wayne Rooney up front, but while Heskey himself never had an issue with it, the Italian's direct approach ruffled many feathers.
"He was very harsh with some things. He'd scream and he'd shout, which I was fine with, because I'd been in and around that environment anyway in academy football, but some people couldn't really deal with that, and they didn't like it.
"I'd frustrated him a couple of times and he'd screamed and he'd thrown stuff."
Ultimately, Capello's approach wasn't a successful one, with his side barely surviving the group stage in South Africa after draws with the USA and Algeria before losing 4-1 to Germany in the round of 16.
While Heskey feels that the 2002 edition was the more successful of the two World Cups that he played in though, he puts that down to the quality of the players more than the differences between Eriksson and Capello.
"I think it was just better playing quality to be honest with you," he responds when asked why things went better in 2002.
"We had some really, really top players. I'm not saying that we didn't at this one (2010) as well, but I just felt that we had a little bit more in 2002."
That era of the English national team is largely viewed as a disappointment, with what was coined a Golden Generation never getting further than the last eight at a World Cup or European Championship, also falling at that stage in 2004 and 2006.
However, Heskey doesn't entirely agree with that assessment, arguing that plenty of other major nations were equally as strong at the time, picking out the talent that France, Portugal and Brazil had to call upon: "Everyone had their own golden generation at that time."
That being said, he can't help but wonder what could have been for him and his fellow members of the class of 2002 in particular.
"I think that was the closest we ever got."