At the beginning of Toy Story, Woody and Buzz were originally rivals with Woody showing jealousy toward Buzz for apparently being replaced as Andy's favorite toy and Buzz thinking himself to be a real space ranger. Their misunderstanding of each other eventually leads them to being separated from Andy, captured by Sid, and subsequently taken to his house. When Buzz finally finds out that he is a toy, he becomes too depressed to help Woody, but Woody gives him words of encouragement and Buzz comes to terms with what he truly is. After Buzz is taken outside to be blown up by Sid, Woody pleads with the Mutant Toys residing in Sid's room to help him rescue Buzz. Following a successful rescue operation, Buzz thanks Woody as the two shake hands, initiating their friendship. The two toys then work together to reunite with Andy, and by the end of the film, they become the best of friends.
In Toy Story 2, after Woody is kidnapped, Buzz goes out on a rescue mission to bring him back home. When Buzz catches up with Woody, Buzz urges Woody to head back home, but Woody declines, instead choosing to stay with his group as he has become convinced that Andy will eventually give him away, a decision that upsets Buzz to the point he leaves Woody to contemplate his decision. However, Woody shortly comes to his senses and calls to Buzz to inform that he is going home with him, to Buzz's relief. After returning home following a successful rescue mission, the two toys agree to be there for each other even after Andy outgrows them.
In Toy Story 3, the two have a falling out when Buzz declares that he and the other toys, believing that a now college-bound Andy does not want them anymore, are going to Sunnyside Daycare after being mistakenly thrown out by Andy's mother, which Woody has witnessed. When Woody declares his intention to leave the daycare to go back to Andy, Buzz offers him a handshake, which Woody refuses, upset that his friends have seemingly given up on their owner. After Buzz is reset into Spanish mode, Woody convinces Buzz that the toys are "amigos" to get him to rejoin their side. When Buzz is restored back to normal, Woody, as with the other toys, is joyous that he has returned. After the toys are dumped into the furnace at Tri-County Landfill, Buzz and Woody take hands and glance at each other for what could have been one last time if not for the Squeeze Toy Aliens controlling a giant claw that rescues the toys from the incinerator. Soon after returning home, Buzz and Woody shake hands, unable to admit that the two best friends are separating ways after all they had been through. However, Woody leaves the note for Andy telling him to donate the toys to Bonnie, and after they are handed down to her, Buzz comforts Woody as they accept that their lives with Andy is complete and begin their new lives under Bonnie's care.
Woody first meets Jessie in Toy Story 2 after he is kidnapped by Al McWhiggin and taken to his penthouse. Jessie is excited that the addition of Woody into the collection of Woody's Roundup, which the two are part of, a complete set to be sold to a museum in Tokyo, Japan, but when Woody declares his intention to return to Andy, Jessie becomes resentful toward him. At one point, Woody, whose arm has been ripped off completely, accuses Jessie of sabotaging his attempt to regain his arm, resulting in a brief fight that is quickly broken up by Stinky Pete the Prospector. After Woody's arm is reattached, Jessie sarcastically allows him to leave, but Stinky Pete insists him to make amends with her. From talking with Jessie, Woody then learns that she once had an owner who grew up and gave her away, a backstory that makes him decide to stay with the group, which brightens Jessie's mood. Later, when Woody has a change of heart, he invites Jessie and Bullseye to come home with him, but Jessie is uncertain whether or not Andy will accept her. It is after Jessie is trapped in a plane bound for Japan when she finally decides to join Woody upon learning that Andy has a little sister.
In Toy Story 3, the two have a falling out when Woody fails to convince Jessie and the other toys that Andy's mother has mistakenly thrown them away as a now college-bound Andy intends to put them into the attic, and the other toys instead choose to be donated to Sunnyside Daycare. At Sunnyside, Woody tries to remind the toys that their job is to be there for Andy, only for Jessie to firmly retort that their lives with Andy is over, to which Woody labels them as selfish before leaving the daycare. During Woody's absence, Jessie learns from Mrs. Potato Head through her missing eye that Andy is looking for his toys, a realization that makes Jessie and the other toys realize that Woody has been right about Andy and decide to return home. When Lots-o'-Huggin' Bear, head toy and warden of Sunnyside, tosses Woody's lost hat in front of the toys, Jessie grows increasingly guilty, fearing that the worst has befallen Woody. When Woody returns to the daycare to rescue his friends, Jessie, as with the other toys, is overjoyed and relieved to see Woody alive and well and apologizes for not listening to him. Remembering that Andy is leaving for college, Jessie and the toys agree to help Woody get back to Andy and then work together to escape Sunnyside. After escaping the incinerator at Tri-County Landfill, Jessie reminds Woody that they are Andy's toys and that their job is to be there for him. Once back home, Woody asks Jessie if she will be okay in the attic, to which Jessie assures him that she will. However, Woody leaves the note for Andy telling him to donate the toys to Bonnie, and after they are handed down to her, Jessie quickly adapts to her new life with Bonnie thanks to Woody's actions.
Woody and Jessie share a sibling-like relationship. The two are shown to have pretty heated arguments from time to time, but they deeply care for each other nonetheless.
- “You're cute when you care.”
- ―Bo Peep[src]
Bo Peep is Woody's love interest in Toy Story and Toy Story 2. In the first film, she offers to get someone other than Woody to watch her sheep, a sign that she plans to spend some intimate time with Woody. After Andy puts more attention on Buzz Lightyear than Woody since the former's arrival, Bo Peep assures Woody that Andy will have a special place in his heart for him. Later, after Woody accidentally causes Buzz to be knocked out of the window, Bo Peep is one of a handful of toys that do not believe Woody had intended to harm Buzz. She is shocked upon learning that Woody has disappeared and starts to worry for him. Later, after Woody reveals himself to be in Sid's room, Bo Peep is relieved to see him, but when Woody inadvertently exposes Buzz's severed arm, she screams in horror and begins to doubt him. On the night before the move, when seeing Andy sleeping sadly in his bed with his cowboy hat, she is shown to be worried about Woody as much as Andy does, suggesting that she still somewhat believes that Woody didn't harm Buzz. On the moving day, Bo Peep is forced to watch as the toys ambush Woody and throw him out of the moving truck, but when Lenny the binoculars sees Woody and Buzz catching up to the truck, Bo Peep uses Lenny to get a closer look and helps the other toys realize their error by telling them that "Woody was telling the truth." At the end of the film, while celebrating Christmas at the new house, Bo Peep wishes Woody a Merry Christmas and kisses him on the face several times.
In Toy Story 2, their interaction is only limited to the beginning and the end of the film. Bo Peep calms Woody down when he becomes frustrated about missing Cowboy Camp for the first year due to his "stupid hat," assuring him that the boy who has written his name on the sole of Woody's boot will take him to camp whether or not Woody has his hat. A little later, after a playtime that results in Woody's arm being ripped and Woody being placed on shelf when Andy decides to leave him home, Bo Peep tries to call to Woody, but Woody instead backs away in depression, leaving her deeply saddened. Later, after Woody is kidnapped from a yard sale, Bo Peep is devastated that someone would steal Woody. Before Buzz leaves on rescue mission to being Woody back, Bo Peep gives Buzz a kiss on a cheek that is for Woody when Buzz finds him. After the toys return home following a successful rescue operation, Bo Peep is more than happy that Woody is safely home.
By the time of Toy Story 3, Bo Peep had left the group. While Woody goes over the toys that he and his remaining friends had lost, Rex mentions Bo Peep, to which Woody reacts sadly, showing that he is still heartbroken over her loss. The upcoming Toy Story 4 will focus on Woody's quest to reunite with Bo Peep.
- “I knew you were right all along, Woody. I never doubted you for a second.”
Slinky is one of Woody's closest companions. In Toy Story, Slinky remarks that he has never doubted Woody. Later, when the toys accuse Woody of intentionally knocking Buzz out of the window, Slinky remains loyal to him, believing it was an accident. He is unhappy when hearing about Woody's disappearance. Later, after Woody reveals himself to be in Sid's room, Woody tosses a string of Christmas lights that Slinky catches, eager to let Woody back to Andy's room, but Mr. Potato Head snatches it away. When Woody inadvertently exposes Buzz's severed arm, Slinky looks devastated at what his friend seems to have done. On the moving day, after Bo Peep reveals that Woody has been telling the truth about Buzz, Slinky attempts to help Woody and Buzz back into the moving van, but his coil gets stretched out to the point it breaks.
In Toy Story 2, Slinky is the one who finds Woody's hat. He joins Buzz on a rescue mission to bring Woody back home after Woody is kidnapped by Al McWhiggin. After catching up with Woody in Al's penthouse, Slinky becomes concerned about Woody not joining the toys in going back home. A little later, after Woody has come to his senses, the toys use Slinky in an attempt to fish Woody out of Al's case containing the Roundup Gang.
In Toy Story 3, while at Sunnyside Daycare, Slinky comments on Woody's truthfulness upon learning from Mrs. Potato Head through her missing eye that Andy is looking for his toys. When Woody returns to the daycare to help his friends escape, Slinky is among the happiest to see his loyal friend return and assists him in subduing the Monkey who monitors the daycare's security cameras. After escaping the incinerator at Tri-County Landfill, Slinky, along with Hamm, is vocal about getting back at Lots-o'-Huggin' Bear for his betrayal and almost getting them killed, only for Woody to talk them out of it. Soon after returning home, Slinky bids farewell to Woody, telling him to "have fun at college."
Like Slinky, Woody has a close friendship with Rex, though he can get annoyed with Rex's antics and insecurities on occasion, yet he still looks out for him. In Toy Story, Rex roars at Woody when he's retrieving his doodle pad for the staff meeting in an attempt to scare him, but only succeeds in annoying Woody in the process. Despite this, Rex looks up to Woody and doesn't immediately turn against him when he knocks Buzz out the window, only turning against him under peer pressure. When Woody and Buzz reunite with him and the rest of the toys at the end of the film, his faith in Woody is restored.
In Toy Story 2, Rex's loyalty in Woody remains intact. This is evident when he joins Buzz's rescue team to bring Woody back home after he is kidnapped by Al McWhiggin. After reuniting with Woody at Al's Penthouse, he joins in the attempt to ward off the Roundup Gang, claiming to be one of Woody's friends. When Woody refuses to go back home with them, Rex is heartbroken, but is later joyous when Woody comes to his senses.
In Toy Story 3, Woody reassures Rex that they won't be thrown away when Andy leaves for college, and they'll always be there for him. When the group ends up in Sunnyside Daycare, Rex tries to persuade Woody that Andy doesn't care about them anymore, only for Woody to say otherwise and leave by himself. When Woody comes back to help his friends escape, Rex is very happy to see him and joins him in the escape plan by subduing Demo Buzz Lightyear with Hamm.
- “Ride like the wind, Bullseye!”
- ―Woody, to Bullseye[src]
Woody first meets Bullseye the horse in Toy Story 2 after he is kidnapped by Al McWhiggin and taken to his penthouse. Bullseye is excited to have Woody join the collection of Woody's Roundup. At one point, as Jessie is about to jump on Woody for accusing her of sabotaging his attempt to regain his detached arm, Bullseye hides in the can and cringes as Jessie beats Woody. He expresses disappointment as much as Jessie does when Woody declares he is leaving as soon as his arm is fixed. After Woody's arm is reattached, Bullseye is still shown to be upset as Woody is about to leave, but brightens up after Woody, having learned about Jessie's tragic past, decides to stay with the gang to go to the museum. Later, when Woody has a change of heart after coming to his senses, he invites the Roundup Gang to come home with him, and when he asks Bullseye, the horse eagerly licks him. Much later, at the airport, after Bullseye frees himself, Woody and Buzz mount Bullseye to rescue Jessie.
In Toy Story 3, after the toys are taken to Sunnyside Daycare, Woody declares his intention to leave, and Bullseye decides to follow Woody back home, but Woody persistently insists the horse to stay with the other toys as he doesn't want him to be left alone in the attic, leaving Bullseye heartbroken. Later, when Woody returns, Bullseye is the one who gives him back his hat after it was left behind during Woody's escape.
- “I tried reasoning with you, Woody, but you keep forcing me to take extreme measures.”
- ―Stinky Pete[src]
Woody meets Stinky Pete the Prospector in Toy Story 2 after he is kidnapped by Al McWhiggin and taken to his penthouse. With the addition of Woody, Stinky Pete is eager to be sold to a museum in Tokyo, Japan, now that the Roundup Gang is a complete set, but when Woody declares his intention to return to Andy, the Prospector becomes determined to sabotage Woody's escape at any costs. At one point, while Woody is sneaking up on the sleeping Al in an attempt to take back his torn arm, Stinky Pete, unnoticed by Woody, turns on the TV, waking up Al, and stealthily places the TV remote in front of Jessie's case so that Pete won't be blamed. This results in Jessie and Woody starting a brief fight that Pete quickly breaks up. After Woody's arm is reattached, Stinky Pete manipulates Woody into thinking that Andy will grow up and give him away, making Woody embrace the decision to stay with the Roundup Gang. Later, after Woody declares his intention to stay with his gang to Buzz, who then leaves him to contemplate his decision, Stinky Pete commends Woody, but is unable to cheer him up, as Woody is hurt by Buzz's warning. Shortly thereafter, Woody, having realized his mistake, declares to Pete that he is going home to Andy, and the Prospector, determined to get the gang sold, locks the grate, Woody's only method of escape. At the airport, Woody fights back at Stinky Pete for harming Buzz, but the Prospector reopens an old tear in Woody's arm and threatens to tear him apart when he refuses to comply with his orders. However, Buzz and his rescue squad stun Stinky Pete with flash cameras, and Woody orders them to place him in a backpack that belongs to a child so the Prospector can learn the true meaning of playtime.
- “Where's your kid NOW, Sheriff?!”
- ―Lotso, to Woody, as he gives the toys their death sentence[src]
In Toy Story 3, after Lotso introduces himself to the toys, Woody tries to convince them that they still belong to Andy, and Lotso tells Woody that they are at a place safe from any harm, indirectly insisting him to forget about his relationship with Andy. When Lotso and his gang corner the toys at the dumpster, Woody brings up the subject of Daisy, Lotso's former owner, which only succeeds in upsetting Lotso even further, causing Lotso to reveal his true feelings about being a toy. Following the confrontation that results in Lotso being tossed into the dumpster, Lotso pulls Woody into a dumpster as revenge for humiliating him and foiling his schemes. At Tri-County Landfill, Woody, with assistance from Buzz, helps Lotso escape the shredders and up a ladder leading to an emergency stop button, only for Lotso to shout an insult directed at Woody and leave him and his friends to their deaths in the incinerator. However, the toys are rescued by the Aliens controlling a giant claw, and once outside, Hamm and Slinky express their desire to get back at Lotso for what he has done to them, but Woody convinces them to forget it, asserting that Lotso is not worth it.
Despite their animosity toward each other, however, Woody and Lotso shared some traits such as being in charge of the toys at their location, being deeply devoted to their owners, and ending up being replaced by their former owner. Had Woody let his fear of being replaced get to him, he would have ended up as cruel and evil as Lotso.