| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| He played Robert California on"The Office"&Raymond Reddingtonon "The Blacklist" | James Spader | $800 | DJ | TV ROLES | 2025-04-08 | #9307 | |
| Boston lawyer Alan Shore; Raymond "Red" Reddington | James Spader | $400 | DJ | ACTORS & THEIR TV ROLES | 2019-01-07 | #7901 | |
| This actor was "Pretty in Pink" on the big screen before being pretty as Red on TV's "The Blacklist" | James Spader | $200 | J | TV | 2018-03-06 | #7712 | |
| Alan Shore &Red Reddington | James Spader | $600 | J | THEIR TV ROLES THEN & NOW | 2015-04-09 | #7044 |