There was a time when Jesse James was practically on top of the world. He had a hit reality series. He ran a successful motorcycle business. And he married a true Hollywood A-lister. Surely, nothing could wrong. Well, as it turns out, everything could.

For the reality star, it seemed that having it all wasn't enough. In fact, it appears that James did everything imaginable to derail his career and destroy his reputation. Things came to a head in 2010 when a woman came out, claiming to have had an affair with James. After that, similar revelations followed.

Looking back, there were at least 10 women that were allegedly involved with the reality star. Find out who they were, along with five women that James had actually dated:

15 Urban Legend: Michelle "Bombshell" McGee

Michelle “Bombshell” McGee is a tattoo model and stripper who claimed to have had an affair with James while his then-wife, Sandra Bullock, was filming “Blind Side.” Moreover, McGee also claimed that James marriage to Bullock was staged. Dani Madrano, who had employed McGee, told Inside Edition, “Michelle told me that Jesse said that the marriage between himself and Sandra Bullock was a sham and that it was just for PR purposes.”

14 Urban Legend: Brigitte Daguerre

Another woman who claimed to have had sexual relations with James was Los Angeles-based photographer Brigitte Daguerre. Daguerre was hired by James in 2008 to do some styling work for a West Coast Choppers photo shoot. In the end, however, the two ended up exchanging some steamy text messages. They also reportedly engaged in sex four times, according to a report from TMZ.

13 Urban Legend: Myla Harris

Myla Harris is a hairstylist who claimed that she has had inappropriate relations with James while already married to his current wife. During an interview with In Touch Weekly in 2017, Harris claimed that James had repeatedly invited her to the Texas home that he shares with wife Alexis DeJoria. During the interview, Harris also claimed that she had sent James “10 or 12” naked photos of herself during their social media exchange.

12 Actually Dated: Janine Lindemulder

Janine Lindemulder is among James’ ex-wives who has always been more than aware of James’ cheating ways. “He’s a chronic cheater,” Lindemulder told In Touch Weekly. Moreover, she said that he discovered his cheating when James accidentally sent her a text message that was originally intended for a mistress. Around this time, Lindemulder says that they had only been married for weeks.

11 Actually Dated: Sandra Bullock

Sandra Bullock is one actress and ex-wife who had had to endure the humiliation of James’ cheating allegations out in public. In the wake of the scandal, Bullock was spotted moving out of the home that she once shared with the reality star. Moreover, she also decided to cancel an appearance for her award-winning movie “The Blind Side” due to the scandal.

10 Actually Dated: Kat von D

At one point in her life, Kat von D was happily engaged to James. But their relationship suffered severely after more of James’ cheating allegations came to light. Von D even took to Facebook saying, “Today I encountered the 19th girl to add to the list of people Jesse cheated on me with during this last year. I kept going back and forth in my mind as to what the best way would be for me to release and let go of any residual feelings remaining from that toxic relationship.”

9 Urban Legend: Deann McClung

Deann McClung was a former West Coast Choppers employee who James hired to work at the business’ Long Beach store in 1999. According to McClung, James allegedly propositioned her and proceeded to make sexual advances. In April 2000, McClung filed an “employment complaint” against James. In return, James sued McClung. According to People, her case was then dismissed “with prejudice.”

8 Urban Legend: Unidentified Dancer

At the height of James’ scandal, more women started coming forward. And it also became apparent that James regularly hooked up with strippers. In fact, according to a report from Radar Online, one woman that James became involved with was a dancer that he spent a lot of money on, even flying her on a private jet. A source also told the publication, “Jesse and the girl he was with at the time got comfortable at the back of the plane. They were definitely having sex and didn’t care who saw or heard them.”

7 Urban Legend: Single Mom

Another woman that James reportedly dated in secret was an unidentified single mother. According to a report from the New York Post, she was a 32-year-old woman who was smitten with the reality star. A source also claimed that this mom would “drop everything” and meet with James at the garage for “nooners.”

6 Urban Legend: Unidentified Female

According to several reports, James was actively seeking the company of other women while he was married to movie star Sandra Bullock. And often, he would rendezvous with the women in his private office at West Coast Choppers. One source even told National Enquirer, “One girl said Jesse would take her into his office and lock the door, while Sandra was in the garage.”

5 Urban Legend: Merilee Gerth

According to a report from TMZ, Merilee Gerth was a former vice president of West Coast Choppers who became intimately involved with her boss. Several reports also indicate that Gerth had kept concrete evidence of her affair, namely a shirt with James’ DNA. Around the time that James’ cheating scandal broke, it was also revealed that Gerth filed a sexual harassment case against the reality star and his company. This was eventually settled out of court for a reported amount of $725,000.

4 Urban Legend: Melissa Smith

While several women who had been allegedly involved with James chose to remain unidentified, there were also several who came forward and revealed themselves. One of which was stripper Melissa Smith. Smith claimed that she had sexual intercourse with James inside his office. According to the Huffington Post, Smith also claimed that her sexual tryst with James lasted for two years.

3 Urban Legend: Valentine Skittles

Valentine Skittles is a stripper who claimed that she had engaged in sexual relations with James, along with tattoo artist Eric McDougall. Both claim that they had engaged in a foursome with James and mistress Michelle McGee. Moreover, during an interview with Life & Style magazine, Skittles also revealed that James had engaged in sex with her without any protection.

2 Actually Dated: Karla James

Karla James is James’ first wife. The two were married from 1996 to 2002, according to E! News. They also share two children, a daughter named Chandler and a son named Jesse Jr. And when the cheating scandal broke, TMZ reported that Karla was spotted coming by her ex-husband’s home to care for their children.

1 Actually Dated: Alexis DeJoria

Alexis DeJoria is the most recent woman to ever come into James’ life. She also happens to be his most recent wife. During an interview in 2013, DeJoria told US Magazine, “I can't even tell you — we have so much in common. We just click. I've never had that in a man before. I've never experienced that with anyone before him, so I knew it right away. He was definitely the one. It has been amazing.”

Reference: TMZ; People Magazine; US Magazine