Here we go again with Timothy Timberland. Mosley has been making hits since the ’90s, and throughout the years, Monique has been right by his side. They started off as a power couple, but their marriage eventually went up in flames. Now, spicy allegations about Timberland’s love for his former collaborator Aaliyah are making headlines. Monique reveals, “I want to give up a little secret. I was in love with him.” This is going to be messy, isn’t it?
For those who hate everything we do on our channel, let me tell you, if we keep bumping heads, one of these days, we’re going to block you. But for those who love and support us unconditionally, it’s time to sit back, relax, and enjoy some Applewood smoked bacon jerky, green apple licorice, or gummy sour peach rings from rrgsnacks.com.
Now, let’s take a trip back to 1993. After her uncle, music executive and manager Barry Hankerson, introduced her to R. Kelly, she and R. Kelly teamed up to record her debut studio album, “Age Ain’t Nothing But a Number,” which was released in May 1994.
She wasn’t talking to Timberland anymore, and I think she and Missy had a falling out too. But despite all that, there was still love between us. Sometimes the business, especially when you’re young, can just pull people apart.
On August 25th, 2001, Aaliyah and eight others tragically died in a plane crash. The entire world was devastated, including her former collaborators. Timberland told MTV’s TRL, “Me and her together had this chemistry. I kind of lost half of my creativity to her. It’s hard for me to talk to the fans right now. Beyond the music, she was a brilliant person, the most special person I ever met.”
He fell into a deep depression for years and his weight shot up to almost 400 lbs. In an interview, he said, “Who wants to be a 400 lb black man? I’m looking in the mirror, and my chest is bigger than a girl’s.”
In 2003, while at an event in Jamaica, he saw public relations executive Mo’Nique Idlet. He said, “When I first saw her, I thought, ‘That’s the girl I’m going to marry,’ because she reminded me of Aaliyah. But then I was like, Aaliyah who? I thought I saw a ghost. She doesn’t look like Aaliyah at all. Somebody get him some glasses.”
Timberland made his move and asked Mo’Nique if she wanted to go to his hotel for a party, but she turned him down. Still, they kept in touch through email after the trip. Even though there was a connection, Mo’Nique said their first date was a bit of a letdown.
They went out to dinner, and Timberland invited all his friends. When they arrived at the restaurant, as she was unbuckling her seatbelt, Timberland was already out of the car and walking across the street. “What a gentleman. Chivalry isn’t dead after all. Just gonna leave your girl behind, huh? Okay, all right.” Eventually, Mo’Nique told him she didn’t think they should date anymore, and Timberland fired back, saying she was too high maintenance. He knew Mo’Nique wanted to be courted, and he replied, “I’m not doing all that crazy stuff. I bet you would have done it for Aaliyah, huh? I bet you that.”
Despite this, the attraction remained, and Mo’Nique continued seeing him. But she soon realized there was something preventing them from taking things to the next level. She said, “It was easier for him to be disconnected than to commit to me.” While they were dating, she used her expertise to help him launch Mosley Brands and Mosley Music Group. Timberland was so impressed with her work that she eventually became the CEO of both companies.
In 2007, they found out they were expecting a baby. According to InStyle, Timberland proposed at the baby shower with a 12-karat canary yellow diamond engagement ring. Their daughter Rain was born in November 2007. They planned to get married within the next year, and Timberland was the one pushing to hurry up and tie the knot. However, his mom wasn’t completely on board with the whole thing.
His mom admitted she wasn’t happy because she didn’t think Timberland was ready to settle down, and she didn’t want Mo’Nique to get hurt in the long run. She better listen to Mama. Mamas know their sons, okay? She’s trying to save you, girl. Don’t do it. Don’t do it.
After five years of dating, Timberland and Mo’Nique got married in June 2008 on a private island. He called the wedding the best time of his life, but trouble was right around the corner. Here we go, here we go.
In August 2010, Timberland called his brother-in-law, deeply upset about a theft that occurred at his Malibu home the day before. One of the things that was eating at him was the theft of his $2 million watch. Timberland reportedly suspected that someone he trusted stole the expensive timepiece. Since there was no evidence of a break-in, he left his residence in his Escalade sometime on August 25th, 2010, and his family became extremely worried that Timberland would take his own life over a watch. What the hell is going on here?
The sheriff’s department sent out squad cars and a helicopter to find him. Thankfully, they were able to locate him. Paramedics evaluated him, placed him inside a patrol car, and took him back home. The details surrounding his disappearance made many people wonder if there was something else going on at the Mosley household.
In December 2010, the Bossip website reported that Timberland was having major trust issues with Mo’Nique, and divorce rumors were swirling.
Rumor has it he discovered she had a secret apartment in Atlanta, and that really got under his skin. Not just some crash pad, but a whole hidden place. Apparently, Timberland also found out she hadn’t been honest about her dating past and conveniently left out the fact that she once dated another producer. Guess who? Here’s a clue: he’s about 5’5″ and from Atlanta. Yep, Jermaine Dupri. Timberland was reportedly heartbroken when he learned the truth.
And about that missing watch? Sources say one of Monique’s family members might have taken it and sold it to someone in Detroit. Sounds like a messy situation, right? In a July 2013 interview with Revolt, Timberland talked about other artists releasing songs featuring posthumous appearances from Aaliyah. He was pretty adamant that these projects would never work out: “It won’t work. Dr. Go do the record. It ain’t going to work ’cause Aaliyah’s music only works with its soulmate, which is me.”
Timberland told E! News, “It’s probably hard to be married to me. It’s not easy. I’m a musical genius. I’m weird. I do crazy things. It’s not like the average norm. But I’m a loving guy.” Monique seemed to agree, as she filed for divorce in October 2013 after five years of marriage. According to a gossip website, Timberland had been unfaithful, and Monique had had enough. There were even rumors of a secret affair in Atlanta.
TMZ reported that Monique asked for monthly support from Timberland to care for their daughter and her son from a previous relationship. Timberland had always treated him like his own, so she felt he should continue to support him. Monique also requested a life insurance policy with her as the beneficiary, alimony, private school tuition, and funds for vacations and summer camp. At one point, she was so financially strained she had to borrow money from a friend to pay her attorney fees.
A year later, the couple called off the divorce, with some noting it might have been cheaper for Timberland to stay married. After reconciling, Timberland hired Monique as his business manager just in time for his work on the show “Empire.” However, their happiness was short-lived.
Timberland opened up to Rolling Stone about his decade-long struggle with pill addiction. It all started after he was shot as a teenager, leading to nerve issues that required prescription painkillers. Later, his poor eating habits resulted in a root canal, and by his 30s, he was taking even more pills to cope with the pain. He admitted that the pills made him sleep all day and say wild things during interviews. Jay-Z had to step in, telling him to stop doing interviews because of the outlandish comments he was making.
Around 2014, Timberland nearly died from an overdose, and in June 2015, Monique filed for divorce again, according to The Jasmine Brand. Timberland ignored the divorce proceedings for months and missed court dates. He told Rolling Stone that his crumbling marriage pushed him into a deep depression. He hadn’t had a major hit since working on Beyoncé’s 2013 album and was frustrated by the rise of minimalist beats from artists like Future and Migos. He told Entertainment Tonight, “Music is a gift and a curse. Once you’re not popping, it messes with your mind.” The pills helped him escape the turmoil. Eventually, his divorce was finalized, though the terms were kept private.
His lawyers accused him of dodging a $440,000 bill, which Timberland finally paid off in July 2017. That same year, the IRS hit him with a $3.8 million tax bill. To add to his troubles, he was diagnosed with pre-diabetes. Timberland admitted to Men’s Health that painkillers made him feel like everything would be okay. “They put me in a great place of not caring, just feeling free,” he said. “I was traveling, doing shows, having fun, just being ignorant.”
In 2017, he began dating Michelle Dennis. Timberland still wasn’t in a good place, and Michelle was worried about him. She told Rolling Stone that his pill usage was so high she feared he might die in his sleep. But Timberland managed to overcome his addiction and got into the best shape of his life. He and Michelle started working out twice a day, and he adopted healthier eating habits.
“Another hard day’s work, baby girl,” he said. “You see the results, we’re TR, that’s right.” As of now, Timberland and Michelle have been together for seven years, although they haven’t tied the knot yet