At that time, Shetty was only 15 and wanted to become a ramp model but she didn't get in because she was only 5'7" and not as skinny and tall as other models. Shetty was heart broken when they rejected her. But Shetty became couple of inches taller later.
Shetty had no background in acting, but at the age of 17, she was offered the leading role in her first film "Gaata Rahe Mera Dil" opposite Rahul Roy. But sadly the film never got completed and was stalled. But the offer didn't stop there, the next film Shetty was offered was Baazigar, opposite Shahrukh Khan and Kajol. Which became a super hit and Shetty earned a Filmfare nomination for Best New Comer.
Next, Shetty signed two films with Govinda and both flopped and things seem to get worse. But it was her one song 'Churake Dil Mera' in Main Khiladi Tu Anari opposite her ex-boyfriend Akshay Kumar, which completely gave Shetty a new image in Bollywood. Shetty became the hottest thing ever to happen in Bollywood and she recieved more praise for her (5'10") body than her performances. Shetty's films flopped one after the another and at one point, she thought of quitting.
By that time, Shetty had already worked in couple of films in Telugu and Tamil. Then Shetty signed Pardesi Babu opposite Govinda and Raveena Tandon. The film flopped but Shetty won the 'Best Supporting Actress' award at the Zee Gold Bollywood Award.
Again, another two films, "Jaanwar "and "Lal Baadshah," flopped. By then the industry had written off Shilpa until her special appearance song 'Main Aayi Hoon U.P. Bihar Lootne' brought her back. The film "Shool "became a hit and Shetty's song spreaded like a wild fire.
In 2000, Shetty starred opposite Akshay Kumar and Sunil Shetty in director Dharmesh Darshan's "Dhadkan." The film that redefined Shetty. Shetty was finally noticed for her acting abilities. Shetty earned a IIFA (International Indian Film Awards) award in the 'Best Actress' category. The film itself became an average at the box office.
Then followed some hit films like "Kushi" (Tamil), "Preethsod Thappa" (Kannada), and "Indian" (Hindi).
In 2002, Shetty had five films ready for release: "Badhaai Ho Badhaai," "Chor Machaaye Shor," "Hathyar," "Karz," and "Rishtey." Sadly all the films flopped and even worst, Karz and Rishtey released on the same day. But not everything was sad in 2002. In Hathyar, Shetty bagged more praise for her role than her co-star Sanjay Dutt. And in Rishtey, Shetty was reported as the only good thing about the film. Shetty recieved two nominations in the 'Best Comedian' category, one by the Screen Awards and the other by Sansui Viewers Choice Movie Awards. And Filfare nominated Shetty in the Best Supporting Actress category.
Shetty recieved mixed reviews in 2003 for her role in "Darna Mana Hai" and her film with Ravichandran Ondagona Baa (Kannada) became a hit.
Shetty's first release in 2004 was director Punit Issar Garv, opposite her close friend Salman Khan. Shetty only had songs in the film, but the film managed to became a hit. Then came director Revathy's "Phir Milenge" opposite Abhishek Bachchan and Salman Khan. "Phir Milenge" dealt with HIV/AIDS issue where Shetty played the victim (Tamanna) of an HIV positive. "Phir Milenge" changed every critics image of Shetty. She recieved great reviews for her performance. Shetty was awarded by the Giant International Award for "Phir Milenge." Indo-Pak's Young Achiever also awarded Shetty.
In 2004, Shetty was nominated in the 'Best Actress' category at every award ceramony, including Filmfare, IIFA, and Screen Awards to name a few. But in a film industry where the 'popular' people rules, Shetty was ignored yet again by every single award ceramonies.
In 2005, AAHOA awarded Shetty for her role in "Phir Milenge." Shetty appeared in director Deepak Tijori's "Khamosh" where she played a call-girl. Shetty was cast opposite her sister Shamita Shetty in "Fareb" alongside Manoj Bajpai and also directed by Deepak Tijori. Shetty also appeared in the multi-starrer "Dus," directed by Anubhav Sinha. Shetty managed to over shadow the guys in "Dus" with her actions, especially the high kick. Recently Shetty's film "Auto Shankar" opposite Upendra was released and is doing great at the box office.
Currently, in Mumbai, Shetty is an AIDS activits and she's also representing PETA India against animal cruelty.