In Rashid Masharawi’s film ‘Eid Milad Laila (Laila’s Birthday, 2008), the viewer accompanies Abu Laila, a judge-turned-cab driver, as he navigates his way around Ramallah, transporting passengers who run the gamut from ex-convicts to young lovers to the sick and underprivileged. On this particular day, he must conduct his daily visit to the Ministry of Justice to follow up on his work permit, transport passengers, and purchase a cake for his seven-year old daughter Laila—making sure that he is home by eight o’clock, in time for the festivities. In a similar manner, in Annemarie Jacir’s film Wajib (Duty, 2017), Abu Shadi must drive around the city of Nazareth with his expatriate son Shadi, hand-delivering wedding invitations for his daughter Amal’s wedding and meeting with Amal during her break so they can go dress shopping. Like Abu Laila, Abu Shadi and his son must navigate heavy traffic jams, decaying infrastructure, and disorderly conduct by other pedestrians and drivers—all the while dealing with their own personal drama. Their family drama revolves around Shadi’s refusal to succumb to his father’s desire that he abandon his current girlfriend, move back from Italy, and settle down in Nazareth—ideally after marrying a decent local woman. Engaging with critical film studies by scholars including Nadia Yaqub, Hamid Naficy, and Hamid Dabashi, as well as humor studies, I argue that Masharawi and Jacir employ the trope of the tragicomic ride as a means of juxtaposing familial and national drama and demonstrating the porous nature of the private and public spheres for Palestinians who must endure and circumvent Israel’s ongoing efforts at extinguishing their personal agency as well as their collective “dreams of a nation,” to use Dabashi’s term. The paper demonstrates that the urban road trip serves multiple purposes, including: revealing the absurd material and political conditions endured by Palestinians, as manifested on the street and in spaces likes homes, cafes, and car-repair garages; documenting the mundane and creative, planned and unplanned, acts of sumuud (steadfastness) in the face of national trauma and daily chaos; and demonstrating the intricacy and diversity of the socio-political landscape inhabited by Palestinians, including those who left, stayed behind, or returned to the homeland.