How celeb photographer had gun drawn on him by Tom Cruise's crew

EXCLUSIVE: Celeb paparazzi reveals how he had gun drawn on him by Tom Cruise and Katie Holmes’ security crew, slept in a shack with a drug lord while searching for Johnny Depp and missed out on first photo of Michael Jackson’s family

  • Phil Penman spent 15 years in New York City as a celebrity photographer, shooting Tom Cruise, Katie Holmes, Madonna, Johnny Depp, Britney Spears, Mike Tyson and countless others
  • The British photographer sat down for an exclusive interview with DailyMailTV and opened up his newly released photo book – Street – to tell his wild tales of working as a paparazzo 
  • He had a gun drawn on him by Tom Cruise and Katie Holmes’ security crew after they tried to divert him from learning where they were staying
  • Penman biked 500 miles a week chasing down celebrities through New York, once taken on a wild goose chase by Madonna’s security detail who were having a secret bet on if he could successfully trail them 
  • He revealed the hardest celebrities he had to shoot were either Mary Kate and Ashley Olsen or Michael Jackson
  • He admitted the shot he regrets missing the most would have been the first photo of Jackson’s family
  • The pap unknowingly enlisted the help of a top Caribbean drug lord while trying to get pictures of Johnny Depp filming the first Pirates of the Caribbean movie, spending the night with the dealer in a shack 

Phil Penman has had a gun drawn on him, unknowingly enlisted the help of a top Caribbean drug lord and has spent countless hours hiding inside cars covertly communicating to partners, waiting for his target.

UK-born Penman is no undercover agent, although most of his work would seem straight out of a spy novel.

In reality, he’s worked 15 years as a paparazzo, biking thousands of miles throughout New York City chasing down celebrities, spending nights holed up in a shack in St. Vincent searching for Johnny Depp and roaming hotels looking for A-listers.

It took Penman, 45, roughly a year to sift through thousands of his photos to curate his recently released photo book, Street, which showcases his celebrity photos, as well as street photography and landscape snapshots. 

In an exclusive sit-down with DailyMailTV, Penman pulls out his book to tell his wild tales of being a celebrity photographer and revealed his biggest regret is missing what would have been a massive shot – the first photo of Michael Jackson’s family.  

Phil Penman spent 15 years in New York City as a Hollywood pap, shooting Tom Cruise, Katie Holmes, Madonna, Johnny Depp, Britney Spears, Mike Tyson and countless others. In an exclusive sit-down with DailyMailTV, Penman pulls out his book to tell his wild tales of being a celebrity photographer, and revealed how he regrets missing what would have been a massive shot – the first photo of Michael Jackson’s family. Pictured: Michael Jackson and a younger boy in Aspen 

The UK-born photographer unknowingly enlisted the help of a top drug lord in the Caribbean while trying to track down Johnny Depp, who was shooting the first Pirates of the Caribbean film – staying the night in a shack, paying the owner with a pack of cigarettes 

Penman recalled a close call when dealing with Tom Cruise and Katie Holmes’ security team. At the height of the buzz around their relationship, Penman said they were the biggest celebrity couple he’s worked on, adding ‘it was a very public affair’. The photographer said one night he tried to stealthily follow the couple, only for one of their security detail to draw a gun on him 

Born in a village outside Dorset, England, Penman got his start in photography from his father, who was a photographer, spending countless hours in the dark room. Always fueled by his desire to live in New York, he jumped at the opportunity to work at a photo agency based out of Los Angeles. He was immediately sent out to a celebrity wedding, getting the only image of the bride by sneaking a camera down his pants. By 2000, Penman was finally in New York – where he’s been ever since

Penman said: ‘At the time I didn’t know. It was just a family. We were looking for Jackson. Then reports were saying he had a family – and that there was a young boy with blond hair.’

Born in a village outside Dorset, England, Penman got his start in photography from his father, who was also a photographer, spending countless hours in the dark room. 

Around 19 years old, Penman started working at a local newspaper. He then landed a job at Microsoft doing the software company’s employee portraits. 

Always fueled by his desire to live in New York, he jumped at the opportunity to work at a photo agency based out of Los Angeles. Upon arrival, he was immediately sent out to a celebrity wedding, getting the only image of the bride by sneaking a camera down his pants.

It took Penman roughly a year to sift through thousands of his photos and curate his recently released photo book, Street , which showcases his celebrity photos, as well as street photography and stunning landscape snapshots

By the early 2000s, Penman was finally in New York – where he’s been ever since.

Penman prefers to shoot portraits and street art, but he said photographing celebrities is what paid the bills, so that’s what he did.  

While he did spend hours chasing stars through the streets of Manhattan, counting down the minutes for a celebrity to emerge from their hotel – Penman was also flung to tropical distentions. 

He was sent to St. Vincent in the Caribbean to find Johnny Depp filming the first Pirates of the Caribbean movie. After driving around the island for hours, Penman was about to give up until a stranger asked for a ride up the road. 

He said: ‘As I start driving up the road, he’s like, ”Okay, so why are you really here?” I said, ”Well, actually, I’m trying to photograph Johnny Depp for this movie, Pirates of the Caribbean”. He said, ”Never heard of it.”

‘I say to him, ”Well, I’m trying to find him, he’s a very famous actor.” He said, ”Oh, you mean starboy?”

‘I’m like, ”Okay, if that’s what you mean.” He said, ”He’s staying on private yacht. I’ll show you where it is.”

‘Bear in mind, we’re in the middle of nowhere. It’s not a built up area. I’m driving with this guy down this dirt track, nothing else around. I’m wondering if I’m going to come out alive, but I’m kind of young, kind of stupid.’

But the man pulled through and led Penman to where Depp was staying, even finding them a spot to spend the night.  

Penman said: ‘I spent the night in this little shack with lizards crawling up the walls because it was too far and too dangerous to drive my car back to the town. I had a bucket in the corner for a toilet.

‘The next day, we got up at 5am, maybe 4am and were crawling through a river. I’ve got my arms above my head, carrying my cameras. We go to this wooden shack on this hill where he knew the owner.

‘He gave the guy a packet of Marlboro cigarettes to use his shack so we could get a vantage point looking down on the boat. 

‘I spent whole time basically looking through this window and there’s a yacht out there. We ended up being able to get these pictures of Johnny on the back of his yacht.’

Penman was sent to St. Vincent to get photos of Johnny Depp filming the first Pirates of the Caribbean movie. After driving around the island for hours, Penman was about to give up until a stranger asked for a ride up the road


Penman said he was trying to find Depp, leading the man to show Penman to where Depp was staying. Penman said: ‘Bear in mind, we’re in the middle of nowhere. I’m driving with this guy down this dirt track, nothing else around. I’m wondering if I’m going to come out alive, but I’m kind of young, kind of stupid.’ But he pulled through and led Penman to where Depp was staying 

Depp comes down from the yacht to talk to some fans, even signing some autographs – all the while Penman is sneaking photos from the shack 

Penman said: ‘I spent whole time basically looking through this window and there’s a yacht out there. We ended up being able to get these pictures of Johnny on the back of his yacht’

Pleased with the photos, Penman said he figured he’d hang out with his new friend, driving around the island and taking personal photos, but while cruising around, a car sped by and took off his rental car’s side mirror. 

He said: ‘We were driving and this car comes flying over this hill. It skids and barely misses another car and breaks to a halt. 

‘These two guys jump out of the car. They don’t look like nice characters. I’m sh**ting myself and my guy gets out and he jumps up. They see him, jump in the car and tear off like crazy. He explains to me they were drug runners.

‘They pick up drugs on the side of the island and then they race them to wherever they need to get.’

Penman said the man insisted that he call the police to document the accident, otherwise he would be charged a small fortune from the rental car company. 

Policemen on the scene began questioning Penman about how he knew his new friend. 

He said: ‘A policeman comes up to me, ”Do you have any idea of the guy you’re with? He’s a really, really bad man. He’s the biggest drug lord on the island, by the way.”

‘They wanted me to explain why I was with this guy. I paid him a bunch of money to help me out while I was on the island. I basically was paying his bail money, because he’d been inside the cell before I met him. His face was all beaten up when I picked him up.’

But despite their warning, Penman took him up on his offer to have his friends fix his damaged side mirror in order to avoid a fee from the rental car company.

He said: ‘They cut a mirror. They were in the middle of this rainstorm just so that the rental car company wouldn’t realize my car being smashed.’ 

Penman said: ‘I spent the night in this little shack with lizards crawling up the walls because it was too far and too dangerous to drive my car back to the town. I had a bucket in the corner for a toilet’ 

Pleased with the photos, Penman said he figured he’d hang out with his new friend, driving around the island and taking personal photos, but while cruising around, a car sped by and took off his rental car’s side mirror. Penman learned men were drug runners and he needed to call the police to document the accident, in order to avoid a fine from the rental car company. While the officers were investigating, one told Penman that his new friend was a drug lord on the island

But despite their warning, Penman took up him up on his offer to have his friends fix his damaged side mirror, in order to avoid a fee from the rental car company. He said: ‘They cut a mirror. They were in the middle of this rainstorm just so that the rental car company wouldn’t realize my car being smashed’

Finding out where a star is staying is one task, capturing them is a whole other beast.

Madonna, for instance, was notoriously hard to shoot. Once, her drivers led Penman around a crazy chase around Manhattan, only to realize that she was never even in the car. The security detail told Penman they had a bet going on if he’d be the last paparazzi standing.

But still, Penman said the hardest celebrities he had to shoot were either Mary Kate and Ashley Olsen or Michael Jackson.

He said: ‘The Olsen twins, I don’t know what it is. They just have this cult like beam in their brains. They could spot a photographer, half a million miles away. You had to be really, really good to get a picture of them. I think half the time they were more on top of things than their security.’

Jackson was another feat. Penman said he covered the legendary singer for years and maybe has only four good images of him.

One of the good shots Penman is referring to is a disguised Jackson, who was bundled up in a blue snowsuit with a mask over his face. Penman said they only realized it was the superstar by his large hands. 

He said: ‘We spent about a week trying to find Michael Jackson in Aspen. It was pure luck. We were ready to leave and we saw two guys on a street corner who kind of looked out of place. Something wasn’t right. 

‘So we followed these guys into town. All of a sudden we see another SUV with another two guys in the front. So we park our car to go find somewhere to figure out what’s going on. All of a sudden this guy walks right in front of the car with this kid dressed up like this. My colleague who I’m with was like, ”Oh my god that’s Jackson.” 

‘I was like, ”How the hell would you you know?” He said, ”It’s the hands. Michael has massive hands.” Not to mention the eight security guys that are standing in the distance watching. 

‘We shot these pictures from the back of a moving car. I was in the back of a SUV shooting through a tinted window because we knew if we shot these pictures openly in the street, then… we wouldn’t have our cameras. 

‘We got these pictures and then we very discreetly followed [them]. There was no way we would have found him. He was staying in this massive mansion outside of Aspen. We just got totally lucky.’

Finding out where a star is staying is one task, capturing them is a whole other beast. Penman said the hardest celebrities he had to shoot were either Mary Kate and Ashley Olsen or Michael Jackson. One of the good shots Penman is describing is a disguised Jackson, who was bundled up in a blue snowsuit with a mask over his face (pictured). Penman said they only realized it was the superstar by his large hands

He said: ‘We spent about a week trying to find Michael Jackson in Aspen. It was pure luck. We were ready to leave and we saw two guys on a street corner who kind of looked out of place. Something wasn’t right. So we followed these guys into town. All of a sudden we see another SUV with another two guys in the front. So we park our car to go find somewhere to figure out what’s going on. All of a sudden this guy walks right in front of the car with this kid dressed up like this. My colleague who I’m with was like, ”Oh my god that’s Jackson.” I was like, ”How the hell would you you know?” He said, ”It’s the hands. Michael has massive hands.” Not to mention the eight security guys that are standing in the distance watching’ 

Penman added: ‘We shot these pictures from the back of a moving car. I was in the back of a SUV shooting through a tinted window because we knew if we shot these pictures openly in the street, then… we wouldn’t have our cameras. We got these pictures and then we very discreetly followed [them]. There was no way we would have found him. He was staying in this massive mansion outside of Aspen (pictured). We just got totally lucky’

Despite having thousands of photographs to choose from, Penman can easily pick his favorite shot: Tom Cruise with his daughter Suri. 

He explained: ‘Actually, I was on my day off. I’d always keep a camera with me just in case. I remember walking past his apartment. There was nobody there, no photographers and his SUV was outside the front.

‘And all of a sudden, Tom and Suri come out and she’s in this little red dress. You’d never try to be sneaky with Tom. If he wanted you to give him a break, I would always give him a break, because the guy was so good to us that you’d always get a picture. 

‘I remember he came out the door, he gave me this incredible shot of him. That’s my favorite picture. He just made it so easy for us.’

But Penman did have a close call once when dealing with Tom Cruise and Katie Holmes’ security team at the height of the buzz around their relationship. 

Penman said they were the biggest celebrity couple he’s worked on, adding ‘it was a very public affair’.

He continued: ‘They came to New York and everything was very public. I worked on them from day one to the end. That was probably the most extensive couple I’ve worked on and I enjoyed it. They made it very easy for us, if they wanted to be shot, they wanted to be shot.’ 

However, one time, they didn’t want their address to be known or photographed there. 

Penman said: ‘It was late at night and I was with two other photographers and we’re following them. I’m on a bicycle and this is like 12am. We’ve got one of my colleagues in the car and we’re trying to discreetly follow them. 

‘His SUV pulls over to the side of the road. I go, ”Oh, this must be the address.” I quickly go for my camera and a security guard jumps out the front. He sees me go for my bag. He pulls out a gun.

‘As he pulls out his gun, it just happens to be an undercover police car sat right there. So as he’s pulling out the gun, these cops undercover jump out of their car. They go for their guns thinking something’s about to go down.’

Penman said the security guard quickly stood down and said the couple didn’t want to be followed, and a shaken Penman gladly backed off.  

Despite having thousands of photographs to choose from, Penman does have a favorite shot: Tom Cruise with his daughter Suri. He explained: ‘Actually, I was on my day off. I’d always keep a camera with me just in case. I remember walking past his apartment. There was nobody there. All of a sudden, Tom and Suri come out and she’s in this little red dress. He gave me this incredible shot of him. That’s my favorite picture. He just made it so easy for us’

Penman said Cruise was his favorite celebrity to take photos of because he would always give photographers a good shot

Penman said that out of all the stars he’s come across, Cruise puts his fans first, blocking out time in his schedule to meet them and sign autographs

Penman’s cycling training has won him favor with celebrities’ security teams. He was up in Kent, Connecticut, on a tip that Katie Holmes was shooting a movie there but ended up leaving empty handed. However, Penman decided the quaint town  would be the perfect spot to train – eventually spotting Katie with Suri 


Penman recalled: ‘I’m sat there, I got all these great pictures and the security guard comes up to me and he’s like ”you’re the guy with the bike? We heard about you. If you cause any trouble, we’re gonna make sure you go to the sheriff’s department. You’re gonna be blocked out. ‘And then he said, ”You wouldn’t want your bike get by getting taken away.” And I said, ”All right. I gotta stop you right now, you can frighten me. But you threaten my bike and we have a problem.” Penman said the guard laughed, because it turned out he also was a bike racer

He said he ended up getting great pictures, adding: ‘I remember coming back into New York City and I went off training and I came back with all my bike gear, and I rode by the house just for a laugh and the guy came out the door and he was laughing his a** off. And I was like, ”I’ll see you next week”.’ Penman said he waited a few weeks before publishing the photos to ensure Holmes had her privacy, throwing off other snappers from knowing her location

Still, Penman said Cruise was his favorite celebrity to take photos of because he would always give photographers a good shot. 

Penman said that out of all the stars he’s come across, Cruise puts his fans first, blocking out time in his schedule to meet them and sign autographs.  

Penman said common assumption about the life of a paparazzo is hanging around hot spot clubs, high-end hotels and fancy restaurants, hoping to see a celebrity glide out the doors, and Penman agrees that’s a part of the job.

But he said there’s much more to it than that.

The photographers have to spend hours in blazing heat or freezing temperatures, in pouring rain and heavy snow.

For Penman it was even more extreme, biking from 400 to 500 miles a week chasing down celebrities.

He said: ‘I was a semi pro bike racer as well. I used the cycling as my way of getting around the city. I realized it was pointless having a car. If you’re on your own, you’re going to end up having a thousand dollars in tickets a week.

‘So I used a bicycle and I would ride around the city all day, probably clocking about 40 miles a day, following cars.

‘My typical day was I would go to Central Park in the morning. I do 50 miles training, get home at 8.30am, jump in the shower, get out the door by 8.45am and then ride another 40 miles following cars around all day.

‘I remember Brad Pitt coming up to me on the film set and he said to me, ”So just out of interest, how many miles do you think you’re going to get today going back and forth following me?” I said, ‘Well, how many times are you going to keep going back and forth?”’

Finding out where a star is one task, capturing them is a whole other beast. Madonna, for instance, was notoriously hard to shoot. Once, her drivers led Penman around a crazy chase around Manhattan, only to realize that she was never even in the car


The security detail told Penman they had a bet going, on if he’d be the last paparazzi standing

Penman says while sometimes the job is pure luck, like when he happened to be staying at a hotel in the Bahamas and he saw Britney Spears drinking a Coke soda – despite being sponsored by Pepsi – most of the time it was relying on tips and sources

Penman’s cycling training has won him favor with celebrities’ security teams. 

He was up in Kent, Connecticut, on a tip that Katie Holmes was shooting a movie there but ended up leaving empty handed. While in the quaint town, Penman decided it would be the perfect spot to train.

Penman said: ‘The roads around there were beautiful. I decided that I wanted to come back up and bring my race bike and I was gonna just use it as a training camp. The next day, I knew kind of where she was living – it was a full four-mile climb. I just kept going up and down this climb, basically waiting for her SUV to come down the hill.

‘Sure enough a car comes down the hill, so I turned around, coming 50 mph down this descent into the village. I would quickly put my bike on top of my car, which I had parked in the town, and start shooting pictures of her through the car’s window.

‘I’m sat there, I got all these great pictures and the security guard comes up to me and he’s like ”You’re the guy with the bike? We heard about you. If you cause any trouble, we’re gonna make sure you go to the sheriff’s department. You’re gonna be blocked out. 

‘Then he said, ”You wouldn’t want your bike getting taken away.” I said, ”All right. I gotta stop you right now, you can threaten me. But you threaten my bike, and we have a problem.”

Penman said the guard laughed, because it turned out he also was a bike racer. 

He said he ended up getting great pictures, adding: ‘I remember coming back into New York City and I went off training and I came back with all my bike gear, and I rode by her house just for a laugh and the guy came out the door and he was laughing his a** off. I was like, ”I’ll see you next week”.’  

Penman said: ‘You have to build your luck, it might take five years of working on these celebrities when they realize that, well, actually, that guy’s not that bad. He’s not running in front of my kids at the school or whatever’

Penman said common assumption about the life of the paparazzi is hanging around hot spot clubs, high-end hotels and fancy restaurants, hoping to see a celebrity glide out the doors, and Penman agrees that’s a part of the job. But he said there’s much more to it than that


There has long been the celebrity complaint of photographers hounding them for their shot, saying they were invading their privacy, and Penman said he understands where they are coming from. He said: ‘At the end of the day, you know, I’m running around trying to get pictures of them so I can kind of understand that you’d be annoyed at best’

Penman flips through the book, laughing photos and pointing out various celebrities

The photographers have to spend hours in blazing heat or freezing temperatures, in pouring rain and heavy snow

 While he is no longer in the game, Penman said: ‘It’s crazy to look back at 15 years of your life’

Penman said he waited a few weeks before publishing the photos to ensure Holmes had her privacy, throwing off other snappers from knowing her location. 

Penman says while sometimes the job is pure luck, like when he happened to be staying at a hotel in the Bahamas and he saw Britney Spears drinking a Coke soda – despite being sponsored by Pepsi – most of the time it was relying on tips and sources.

While he is no longer in the game, Penman said: ‘It’s crazy to look back at 15 years of your life’

Penman said: ‘I was doing it for 15 years, working as a celebrity photographer. You have to build your luck, it might take five years of working on these celebrities when they realize that, well, actually, that guy’s not that bad. He’s not running in front of my kids’ face at school.

‘It might be that you’re developing a relationship with a security team. I’ve had before, a security guard for a well-known celebrity say, ”If anyone’s going to get the picture, make sure it’s that guy. He’s the only one who is going to get the picture” because you’ve developed this relationship over the years where you’ve deliberately not shot pictures or you’ve deleted pictures because it’s in the common goal.

‘It’s going to be better for you in the long run than just making a quick hit. I found that over the years that was what worked for me.’ 

There has long been the celebrity complaint of photographers hounding them in attempt to get their shot, saying the paps were invading their privacy, and Penman said he understands where they are coming from.

He said: ‘At the end of the day, you know, I’m running around trying to get pictures of them so I can kind of understand that you’d be annoyed at best.

‘I could understand their point of view if they didn’t want to be shot that day. If you can see that they don’t want to be shot, then a lot of the time, I just find it was best just to leave them alone.’ 

Penman flips through the book, laughing at the portrait of artist Damian Hirst – he had been hungover and thrown up all over his hotel suite’s bathroom, and pointing out various celebrities. 

While he is no longer in the game, he said: ‘It’s crazy to look back at 15 years of your life.’

Source: Read Full Article