Ajay married Kajol when she was bigger star than him.
Aishwariya is much bigger star than Abhishek.
Both current and ex wife of Saif are bigger star than him, Amrita was a top actress in the 80's and Kareena had been ruling BW for 18 years where Saif never established himself as a lead hero in BW.
Even I think Genelia is bigger star than Ritesh because Genelia was a big star in the south and gave a hit movie Jaane Tu Ya Jaane Na unlike Ritesh that mostly always did supporting roles on mostly comedy movies.
The only actor that I know is Akshay that married less sucessful actress than him but Twinkle is first superstar Rajesh Khanna's daughter and that's why Akshay probably married her.
Any other actors that married less sucessful actress than them?
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