15 Most Awkward Celebrity Father-Daughter Photos

We’re all for father/daughter closeness and supportive dads. But for some of these celebs, close can border on creepy and go full into wrong.

Fathers and daughters have a special bond. While popular culture often fixates on the important role that a father figure plays in a young boy’s life, his presence and engagement towards his daughter is just as vital. Research has shown that a father’s role in his daughter’s life can be directly related to her educational and career successes. Women born in the 1970s are three times as likely to pursue the same or similar career fields as daddy dearest, than in previous generations.

We’re all for father daughter closeness, and supportive dads doing whatever they can to help their daughter achieve her dreams. Family is one of the most important things in this world, but in the case of some of these celebrities, close can border on creepy and go full into wrong. When a dad pays too much attention to his daughter’s looks, or talks about it endlessly, it naturally makes a lot of us feel uneasy. Sometimes it's completely innocent, unfortunately other times it's not.  Other times a photo reveals some family tension hidden under the radar. Here are 15 awkward father daughter photos.

15 Ashlee & Joe Simpson

Parents are proud of their children for so many things. And we’re all genetically programmed to think that our children are cute and good looking. That being said, most parents are proud of their children’s achievements above and beyond their “physical assets”. Joe Simpson is a proud dad, but what he likes to boast about most of all gives us the willies, since he loves to talk about and show off his hot daughters and their breasts.  There's no question as to where he's looking in this photo with daughter Ashlee Simpson. To add to the oddity of this, Jessica Simpson has gone on record saying she doesn’t mind his comments. This is also the same man who reportedly gave his daughter a type of “promise ring” to promise to be “the man” in her life until she got married.

14 Liv & Steven Tyler

What’s not to love about Liv Tyler making up for lost time with her dad? She didn’t discover that he was her father until she was eight years old, and it’s nice that they’ve been making an effort ever since to remain close. Sure, it was a little strange that he cast his barely legal daughter as a sex symbol in one of his music videos, but he’s a rock star so we’re willing to let that slide. But when the duo practically made out on the red carpet of the Super opening in LA, and continue to be photographed in very affectionate poses, it got people talking. They seem to have a really tight and loving relationship. Maybe the paparazzi just seem to capture their most affectionate moments?

13 Ashton Kutcher & Rumer Willis

Can you see a school girl crush in this photo? When Ashton Kutcher and Demi Moore began dating, she was 41 and he was 25. Two years after dating the pair married, and Ashton became step dad to Demi Moore and Bruce Willis’ three daughters. In the time that has passed since, Rumer Willis has confessed to having a crush on her former step dad. The star has admitted that it was strange to suddenly move the young heartthrob from a childhood crush to completely off limits. When interviewed on the Howard Stern Show she said, “He was a really great stepfather. The perspective switched quickly. That's when you open up your Teen Beat, you take him down and put somebody else up. I feel like I told my sister that at some point, 'Gotta cross him off the list.'"

12 Miley & Billy Ray Cyrus

Some families are really tight, and that’s totally cool. But posing like a couple instead of a father daughter team, particularly from such a young age, rubs a lot of people the wrong way. When fame hits an entire family perhaps it skews their judgement of what’s appropriate and what borders on creepy in terms of PDA. A sexually suggestive glamor shot for Vanity Fair magazine solo is one thing, but when it’s with your father – just, yuck. During the same shoot Miley Cyrus stripped down further and was draped in a sheet for some other solo portraits. Her father, Billy Ray Cyrus thought the whole thing was a classy affair saying, “I think it's really artsy. It wasn't in a skanky way…” Sure it wasn’t.

11 Morgan Freeman & His Step-Granddaughter

Inappropriate Father/daughter relationships are one thing, but what about inappropriate grandfather –granddaughter ones? A number of years ago rumours circulated that actor Morgan Freeman was having an affair with his step-granddaughter, E’Dena Hines. The actor was in an open marriage at the time, and the star and his step-granddaughter started hanging out with dinners at restaurants, until one night things went too far when the man with the golden voice got so drunk that he tried to get her into bed. Although the pair aren’t related by blood, and E’Dena reportedly asked him to back off and even told his ex-wife, she eventually gave in. After Morgan divorced his wife, other gossip was reported that the pair wanted to tie the knot. Freeman was quick to deny these rumours.

10 Jon Voight & Angelina Jolie

While they’ve taken some great strides at repairing their relationship, it’s no surprise to anyone that Jon Voight and daughter Angelina Jolie have a troubled past. Jon left the family before Jolie’s first birthday and has gone on record on television stating that his daughter had, “serious mental problems”. It was at that point when the rest of the family cut all ties with the actor. They began to talk again six years later when Jolie’s mother fell ill with ovarian cancer. Just the same you can definitely see the strain and discomfort in any picture of the two together. The dad is trying nowadays though. He sent his daughter a video card for Mother’s Day and recently was spotted during a sushi dinner with his daughter and four grandchildren.

9 David & Harper Beckham

The debate is heated on Instagram as to whether or not this photo is sweet or awkward. As a parent to a pair of five year olds, I think it’s a really sweet moment shared; however when David Beckham posted this adorable moment kissing his five year old daughter Harper on the lips on Instagram with the tag “Kiss for Daddy” people freaked out – a lot. Last year, Victoria Beckham found herself under a similar microscope when posting a picture of her kissing Harper on her fourth birthday. One commented, “On the lips what has this world come to?” and another “Not sure about this picture”. He’s a dad who’s not afraid to be affectionate with his little girl – leave them alone!

8 Brooke & Hulk Hogan

It’s been an uncomfortable joke for years now: Wrestling Superstar Hulk Hogan has an inappropriate crush on his daughter, Brooke Hogan. Most grown women wouldn’t ask daddy dearest to rub suntan lotion on their rumps, but apparently in the Hogan family sun safety is really important. He also sparked more controversy when he accompanied his scantily clad daughter to a Maxim photo shoot a few years ago. People were talking about photos taken of and shared by the father daughter duo again when Hulk posted a picture on Twitter with the caption “Brooke’s Legs”. Brooke simply wants all of the haters to “back off” and leave them alone. Meanwhile: we get it Hulk, your daughter’s hot. Can you please stop talking about it for two minutes?

7 Ozzy & Kelly Osbourne

When we think of Ozzy Osbourne we think of the Prince of Darkness biting the head off of a bat live in concert, not him canoodling with his daughter Kelly. Just the same the two shared a rather sweet moment on the red carpet that seems uncharacteristic for the pair of them, or is it? Kelly Osbourne is still clearly a “daddy’s girl” even in the face of controversy. She lashed out on Twitter at her father’s mistress instead of daddy dearest when news of his affair with his hair stylist surfaced, by posting an angry tweet along with the woman’s personal cell phone number. When being called out on this Kelly responded, “Are you in my family? NO YOU ARE NOT YOU HAVE NO IDEA WHAT SHE DID! So keep ur high-mighty opinions to yourself!” Back off, he’s your dad, we get it Kelly!

6 Lindsay & Michael Lohan

While Dina Lohan gets a lot of credit for being the worst of this pair of parents, since she seems to continually encourage Lindsay Lohan’s party hardy ways, it sometimes casts a shadow on what a creep Michael Lohan is. The relationship between the two has always been strained. In fall 2016, Lindsay took to Twitter to slam her father tweeting, “My father is a lunatic & doesn’t even deserve such a title since he’s never been around in my life other than when he’d threaten me & my family,” The Mean Girls star added, “He should be where he has always put himself after verbally abusing and physically abusing people all my life– behind bars.” No wonder this photo of the pair is so incredibly awkward.

5 Donald & Ivanka Trump

Anyone who hasn’t been under a rock for the past several years understands just how outspoken President of the United States Donald Trump can be, saying all of the wrong things. The comments he repeatedly makes about his daughter are enough to make anyone squirm. Like when on national TV he suggested that if Ivanka Trump weren’t his daughter perhaps he’d be dating her. He’s called her “voluptuous”, and he brags incessantly about just how hot she is, and in 2004 he gave shock jock radio personality Howard Stern “permission” to refer to her as a “piece of ass”. Trump has said, “My daughter, Ivanka. She’s 6 feet tall, she’s got the best body. She made a lot money as a model—a tremendous amount.” Such a classy dad.

4 Hulk & Brooke Hogan - Part 2

Some parents provide so many creepy moments for the cameras that they make the list twice. This means it’s not a one off occurrence, they’re regularly making strange choices that paparazzi capture again and again. Not only did the Hulkamaniac marry someone who strongly resembled his daughter, his attempts to look like a regular dad for photo ops just come off as strange and phoney; he’s clearly loving every minute of it. When Brooke posed in the buff as part of a PETA photoshoot, dad was front and centre for the Women in Cages Exhibit “pretending” to be embarrassed for his naked daughter's pictures. Brooke has gone on Twitter saying, “I’m SO sick of people saying me and my dad are in some perverted relationship.”

3 Jon Gosselin & The “Suspicious Behavior” 

It wasn’t too long ago that Jon Gosselin entered our living rooms on reality TV as the frazzled dad of many, many children in the hit TV show Jon & Kate Plus 8. In Touch magazine followed up on a story and found another police report accusing Jon of kidnapping (then 10 year old) daughter Hannah, and a statement from Kate stating, that "she detects suspicious behavior between Jonathan and their daughter.” While none of this has been proven, and Kate has been known to sling mud, odds are people aren’t going to look at photos of the father and daughter the same way for a long time. The reality star admitted last year that he hadn’t seen his children in years. Daughter Mady said, “He should maybe spend some time thinking about why we don't want to see him, and maybe realize that if he ever does want a relationship with us, talking about us on TV is not the way to make that happen."

2 Mackenzie & John Phillips

While it’s easy to speculate about a photo of a Hollywood father/daughter duo, the confessions from Mackenzie Phillips about her relationship with her father are really upsetting. The star admitted that she was part of a decade long “consensual sexual relationship” with her father, John Phillips of the band The Mamas and the Papas. She told Oprah Winfrey that she was raped by her father when she was 18 years old and passed out during a drug binge, but later continued to have relations with him, even after she married someone else. When she found out she was pregnant, fearing the child was her father’s, he paid for her to have an abortion. Phillips shared with Oprah that she confronted her father about the rape, but he painted their relationship as a romantic one. She said, “My dad said: 'Raped you? Don't you mean made love?' In that moment, I thought I'm really on my own here."

1 Donald & Ivanka Trump - Part 2

It’s no surprise that women are often an object of POTUS Donald Trump’s affection or ridicule, particularly how they look. We guess it’s a good thing for daughter Ivanka that he’s so fond of what a fine genetic specimen she is. At one time when he was asked what are both his and his daughter’s favourite things he said, “I was going to say sex, but I can relate to (golf and real estate)”. Shudder. No wonder pictures like this give everyone the heebie-jeebies! Or how about the time he pondered this thinker, "Is it wrong to be more sexually attracted to your own daughter than to your wife?"

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Most Awkward Celebrity Father-Daughter Photos