From 'Hero' upto now Jackie has always been a hassle free and cool actor. This cool attitude has almost always backfired. He is almost always starring in two hero projects and is usually a police inspector or an elder brother - and usually plays second fiddle. But this still hasn't kept the awards away from him. These days he's heavily into B - grade films with Mithun. However his company (JSEL) has announce a few good projects which might just do the trick
He's considered one of Bollywood's most affable stars. So much so, Jackie Shroff is open to fielding questions about everything under the sun including his take on the opposite sex, his own sexuality, his family life, his financial difficulties and then perhaps, his film career! This has been the story of his life, ever since Jackie graduated from being a small-time 'dada' at Teenbatti (in South Bombay) to a popular model, till finally, Dev Anand picked him up for a minor part in Swami Dada (1982).
1973 Jackie Shroff had a small role in Dev Anand?s Heera Panna (1973).
1982 to 1988 In 1982, he was cast in Dev Anand?s Swami Dada but it was Subhash Ghai who gave him the big break with Hero (1983) as Jackie Dada who is a bad guy with a good heart. In Subhash Ghai?s Karma (1986), he played one of the convicts who is hired to take on the villain Dr.Dang.
1989 to 1995 He worked with Ghai again in Ram Lakhan (1989) with Anil Kapoor and Madhuri Dixit. The movie was successful. The same year he played the role of Kishen, a gangster, in Vidhu Vinod Chopra?s Parinda (1989). The movie also starred Anil Kapoor, Nana Patekar and Madhuri Dixit and went on to win several awards. Shroff won his first Filmfare Best Actor Award. Another Ghai movie that starred him along with Sunny Deol and Naseeruddin Shah was Tridev (1989) which again was his third hit in 1989.
After a horror flick 100 days (1991), he played Vishal in Saudagar (1991). Khalnayak, 1942: A Love Story and Gardish were his major releases in 1993. He won the Filmfare Best Supporting Actor Award for 1942: A Love Story.
He won a second Filmfare Best Supporting Actor Award for his role as a movie star who falls in love with an upcoming actress in Ram Gopal Varma?s Rangeela (1995).
1996 to 2002 The J.P.Dutta directed multi starrer Border (1997) saw him as a commander Andy. Ketan Mehta?s Aar Ya Paar (1997) was a murder mystery. He didn?t have any major successes following this until Refugee (2000) and Mission Kashmir (2000).
In Rajkumar Santoshi?s Lajja (2001) he played Manisha Koirala?s wayward husband. In Sanjay Leela Bhansali?s Devdas (2002), he was cast as Devdas? friend Chunni Babu.
2003 to 2009 Jackie Shroff was seen as a murderer in Nagesh Kukunoor?s 3 Deewarein (2003). His other releases were Bhagam Bhag (2006) and Fool and Final (2007).
In 2009, Jackie Shroff will be seen for the first time in a Tamil movie Aaranya Kaandam. His other movie is Veer with Salman Khan in which he plays a villain.