1. Diddy and the one and only Biggie Smalls in 1995. Source: false 2. Diddy all laughs next to Andre Harrell. Source: false 3. Diddy and Mase at the 11th Annual Nickelodeon Kids Choice Awards in 1997. Source: false 4. Diddy and B.I.G. Source: false 5. Diddy flaunting his bling in 1997. Source: false 6. Diddy in a baggy suit. Source: false 7. Diddy in camouflage. Source: false 8. Old school Diddy. Source: false 9. Diddy shining next to Tyra Banks. Source: false 10. The super throwback of Diddy and Lil Kim. Source: false 11. Bow tie Diddy. Source: false 12. Diddy and the kids back in ’04. Source: false 13. Mowhawk Diddy in ’04. Source: false 14. Diddy maxin’ and relaxin’ in all white in 2005. Source: false 15. Diddy with the shiny puffer vest on. Source: false 16. Diddy in all black everything back in ’08. Source: false 17. Diddy nurturing his baby, Sean John, in 2008. Source: false 18. Diddy cleans up nice. Source: false 19. Diddy, the king of branding. Source: false 20. Calm Diddy Combs. Source: false 21. Diddy with Dem Boyz. Source: false 22. Diddy gets his inspirational speech on at Howard University last year. Source: false 23. Diddy, the family man. Source: false 24. Old school Diddy was a ladies man, but Cassie got 2015 Diddy locked down. Source: false 25. Diddy still looking good in 2015. Source: false