<P> Portrayed by Sam Robards in seasons one, two, four and six . Howard "The Captain" Archibald is the father of Nate Archibald . Howard is a white - collar criminal and a recovering cocaine addict . He leaves to escape arrest, still addicted to cocaine and Nate punches his father before the Captain could get into his limo and fled to Dominica . In the second season, when he returned to New York, to take Nate and his mother with him, Nate gave him a choice . Either go back to Dominica and never speak to his family again or turn himself in to the police . Howard decided to do the right thing and chose to turn himself in . In the fourth season, Howard later receives a file for divorce while in jail, a few months before his release from prison . When he is paroled, Howard soon takes a job with Russell Thorpe . </P> <P> Portrayed by Robert John Burke in season one, two, five and six, Bartholomew "Bart" Bass, is Chuck's billionaire father, founder of Bass Industries and was married to Lily van der Woodsen . His family lived at the New York Palace Hotel, which he owned . His money was self - made, as opposed to inherited like most Upper East Side families . He was controlling with his family, ruthless in business and demonstrated little affection for Chuck, and it's revealed that this is because he holds his son responsible for his late wife's death (Chuck's mother died while giving birth to him .) At times Bart appears to care about his son, and asked him to be his best man at the wedding . Bart complimented Chuck on his speech, and said he was proud of his commitment to Blair . In season 2, with Dan's help, he and Chuck try to mend their relationship, but he suddenly dies in a limo accident . In season 3, he reappears as a ghost on the anniversary of his death . In season 5, Diana Payne claims that she is Chuck's biological mother, conceiving him after she and Bart had an affair, but it is revealed to be untrue . When looking for Diana's secret, he is discovered alive . As Life on the Upper East Side goes on with its gossip and rage of others, Chuck finds out something he was not supposed to about his father and how he pays people off to "accidentally" kill people who are after him and with information that could destroy his reputation . As Chuck and Blair keep digging for dirt on Bart, He gets Nate into prison and tries to kill his own son in a flight to Moscow as a deal to Chuck to keep everyone he loves safe . As a party is going on for Bart, it is then announced that there was a plane crash which turns out to be a Bass industries private jet which is the one that Chuck was in . As Dan gives hits heart felt speech about what was supposed to be Bart, Dan reveals it was not Bart he was talking about, it was Chuck as he steps onto the stage and reveals in front of the cameras that his father tried to have him killed . Bart tries to fix the mess that Chuck had done while having him taken to the roof top to the building by his guards and leaves saying that Chuck is going to be put in an institute for his delusional mind set . As Chuck tries to get the truth out of Bart on the roof top, Bart threatens Chuck which leads to Chuck hitting Bart and Bart hanging from the side of the building as Blair approaches the scene . Bart eventually loses grip of the rail and falls off the building without any regret from Chuck and a horrified Blair . </P> <P> Portrayed by Desmond Harrington in seasons two through six . Jack Bass is Chuck's uncle who comes to New York upon hearing of his brother, Bart Bass' death, and slept with Blair on New Year's . Jack headed Bass Industries in Australia and served as Chuck's legal guardian when Bart died . He then plots to take Bass Industries from Chuck and sets him up by having the Board of Bass Industries to witness his debauchery and inebriation . Chuck turns to Lily to remove Jack from Bass Industries due to his incompetence at handling the assets of Bass Industries causes the business to become stagnant . Jack loses hold of Bass Industries when Lily decides to become Chuck's new legal guardian, thereby transferring a significantly large power of the company to her . Jack then confronts Lily while he is high and attempts to rape her until Chuck has him kicked out of the opera . Jack is then sent back to Sydney . By the third season, during Chuck's opening of his new hotel, Blair aids him in getting a liquor license for Chuck by contacting Jack . Chuck confronts Blair for contacting Jack and Blair receives flowers and a note stating that the liquor license is fake . Blair and Chuck eventually allow the police to end the opening party and therefore receive enough press and publicity for future clients for a genuine speakeasy that Chuck has been planning . Chuck goes to find Jack, whom could maybe help him take back Bass Industries from Lily, who is going to sell it . Jack returned to help Chuck in season four . in season 5, Jack, back to New York to thank him for saving his life in the car accident by donating blood, but starts to doubt Jack's story when Chuck investigates and learns that Jack was recently diagnosed positive with Hepatitis C, and a test on Chuck turns to be negative . At the end of episode, Chuck finds out that it wasn't Jack who saved his life and assumes it was Elizabeth Fisher, Jack appears to verify his story by saying that she didn't want him to know . Although, near the end, there is a scene with Jack in his limo calling someone and telling her that Chuck knows that Jack didn't donate him the blood, and that she should come . In prior episodes to episode 22 "Raiders of the Lost Ark", Chuck begins to believe that Jack Bass is more than an uncle and is actually his biological father, but this isn't proved in the episode previously stated . In the series finale, he is shown to be in a relationship with Georgina Sparks . </P> <P> Portrayed by Susan Misner . Alison is Rufus's estranged wife and Dan and Jenny's mother . She had an affair while living and working as an artist in Hudson, and Rufus cannot forgive her for the transgression . She returns for the holidays during the first season, but Rufus asks her to leave after a former lover attempts to contact her at the Brooklyn loft . She and Rufus ultimately end their marriage . </P>

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