And most recently, the music mogul took a trip to the dentist to apply a set of "more natural" veneers on his teeth.
The America's Got Talent judge was pictured with his cosmetic dentist, Dr Apa, on Instagram on Monday, and he looked delighted with his new smile.
VIDEO: Simon Cowell celebrates his birthday with son Eric
In the caption, Dr Apa wrote: "It's official. I'm going to Hollywood! Actually Dubai this weekend. And it's truly amazing working with amazing people. Thank you @simoncowell for putting your trust in us."
Simon Cowell was all smiles as he got a new set of veneers
Fans were quick to comment on Simon's new teeth, with one writing: "Great job, bravo," while another wrote: "Hope this means he's doing well." A third added: "Ooh this is awesome."
According to TMZ, Simon was seeking out a more natural smile to replace his old veneers, and he looked incredibly happy with the results.
The X Factor judge has been keeping a low profile following his accident and has been recovering at home in Malibu with round-the-clock care.
Simon was recently pictured walking during a shopping trip with partner Lauren Silverman and son Eric, showing positive signs of his recovery.
The X Factor judge is slowly recovering following his bike accident
The doting dad also recently celebrated his 61st birthday, and appeared in footage from his birthday meal on Terri Seymour's Instagram account.
Simon was seen sitting at the table dressed in a smart suit, surrounded by his loved ones.
Simon is being looked after by partner Lauren Silverman and son Eric
In the clip, the star's son Eric and Terri's daughter Coco were seen running over to him while singing 'happy birthday' while a friend presented him with a cake.
The music mogul was absent from both America's Got Talent and Britain's Got Talent following his accident, but was never far from his co-stars' thoughts.
Simon is recovering at home in Malibu
Amanda Holden, who took over as head judge in Simon's absence, recently opened up about her friend during an appearance on Loose Women, and revealed that he was doing well, and that she was confident that he would be back on TV in no time.
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