Bobby Chemmanur famously known for his unique ventures and eccentric personality, once expressed a strong desire to understand what life inside a prison is like. Nearly 15 years ago, he approached the Kerala Police with a request to experience jail life firsthand. However, his request was turned down, as the authorities stated that one cannot stay in jail without committing a crime.
Later, Bobby fulfilled this peculiar wish through the Telangana government’s “Feel the Jail” tourism program. For a fee of ₹500, he spent 24 hours in prison. During his stay, he wore a prison uniform, performed tasks assigned to prisoners, and ate the same food provided to inmates. Phones were strictly prohibited. Reflecting on the experience, Bobby stated that he now truly understands the reality of jail life in Kerala. Ironically, though he once paid ₹500 to experience jail, more recently, even spending large sums and hiring top lawyers couldn’t save him from legal trouble.
In another viral video, Bobby claimed to have “10,000 girlfriends.” When asked about this in an interview, he humorously replied, “Even if I fell in love with a new girl every day since first grade, I doubt I could reach that number. Haha… Well, let this be considered a record for me!”
When asked about his family in an interview, Bobby shared, “My family consists of my wife, my daughter, my father, my mother, a brother, and a sister — all in single numbers. My mother, Cecily, comes from an old aristocratic family. She loves me dearly but is also strict. If I do something wrong, she wouldn’t hesitate to discipline me, even now. My father, Devasikutty, is someone I deeply admire and aspire to be like. Even while managing our business, he served in the Air Force for 15 years before returning to the business. He leads a simple life, walking to church and practicing yoga every morning at 5 AM. He once advised me to dedicate at least ten years of my life to serving the country.”Bobby also shared an anecdote about his dream of becoming a pilot. “After college, my father arranged everything for me to pursue pilot training, but my mother was scared and tore up the admission documents, putting an end to that dream.”
Reflecting on his childhood, Bobby mentioned, “I always wanted a bicycle when I was young. Later, it was a bike, then a car, and eventually a helicopter. Once I got all of these, the thrill wore off. Searching for something different, I read a book about Mother Teresa, which inspired me to pursue charity work. It taught me that true love and peace come only through service. That’s how I got involved in philanthropy.”A sports enthusiast since childhood, Bobby practiced high jump, football, running, kung fu, karate, dance, and action stunts. Over the years, his unique endeavors and statements have often drawn both admiration and mockery.
For someone who once eagerly sought to understand life behind bars, Bobby’s recent real-life experience with legal issues has only added to the public’s curiosity and amusement.
