Preheat oven to 350 F. Grease a 9 x 5 loaf pan and set aside. I use the nonstick cooking spray with flour in it.: The kitchen will fill with a warm, faintly sweet aroma once the oven reaches 350 F , and a properly greased pan ensures clean removal and beautiful crust edges. When you grease and flour the pan, rub a little into the corners so the batter clings evenly. This matters because a stick can tear the loaf as you remove it. A common mistake is skimping on grease, which leads to tearing or sticking.
Combine bananas and sugar (both brown sugar and the granulated sugar) in a large mixing bowl and beat until combined. Beat in pumpkin, egg, butter, and vanilla until well combined.: As you mash and beat, you will notice the mixture go from chunky to glossy and cohesive, with the sugars dissolving and the banana aroma lifting. The batter will smell sweet and slightly caramelized from the brown sugar . This step creates a uniform wet base so the pumpkin and butter disperse evenly. Overbeating can overly aerate the batter, but under mixing leaves pockets of dry flour later, so aim for smooth, not fluffy.
Combine the dry ingredients in a small bowl and stir into the wet ingredients until just combined.: The dry mix will be dusty and pale, and folding it in will dull the shine of the wet batter, giving you a thick, pliable mixture. You will hear a slight thunk as the spoon moves through and see streaks disappear when it is ready. Doing this gently keeps the crumb tender, because vigorous mixing develops gluten which gives a tough texture. A common trap is overmixing, which produces a tight, dense loaf.
Pour half of the batter into the prepared loaf pan. Evenly spread the batter to the edges of the pan. Set aside.: The batter will be thick and glossy, and smoothing it to the edges creates an even base layer so the cheesecake ribbon sits uniformly. Use a spatula to coax it into corners and flatten the top. If you leave valleys, the cheesecake may seep into pockets and create an uneven swirl. A troubleshooting tip is to tap the pan gently on the counter to remove large air bubbles before adding the cheesecake layer.
Beat the cream cheese and sugar together until light and fluffy. Beat in the egg and vanilla until combined. Beat in the flour and continue beating until no lumps remain.: The cream cheese should transform from dense to airy and pale, with a soft, whipped texture. You will smell a tangy, sweet aroma as the sugar dissolves. Beating the egg and vanilla in ensures a smooth custard like filling. If lumps remain, press them against the bowl with your spatula to smooth them out. Cold cream cheese makes this step difficult, so warm it first to avoid clumps.
Spread the cheesecake filling carefully over the contents in the loaf pan making sure it's as even as possible.: The filling will be thick and silky, and when spread it should form a pale ribbon across the loaf. Smooth it gently with an offset spatula, watching that it does not sink into the wet batter beneath. Evenness matters for balanced bites; an off center filling can create thin or overfilled slices. If the filling slides, it may be too soft, so return to the fridge briefly.
Spread the remaining half of the pumpkin-banana mixture over the top of the cheesecake filling. Make sure to smooth the top and make it nice and even.: The top layer should match the base in consistency, forming a cohesive sandwich around the cheesecake. Smooth it carefully so the top is even and will brown uniformly. Uneven tops bake unevenly, causing some areas to dry while others remain underbaked; take a moment to level it well.
Bake for 55-65 minutes or until an inserted toothpick comes out clean.: As it bakes, the loaf will rise and the top will shift from glossy to a warm golden brown, releasing a rich aroma of pumpkin pie spice and caramelized sugar. You may hear faint crackling as the top sets. Toothpick testing is essential because oven temperatures vary, so check at the earlier end of the window. Insert gently through the top without touching the cheesecake ribbon, and if it comes out with moist crumbs, it is done. A common mistake is removing too early, leaving the center underdone and gummy.
Let cool in pan for 10 to 15 minutes before removing to a wire rack to cool.: The loaf will deflate slightly as it rests, and the cheesecake layer will firm up, making slicing neater. Cooling in the pan prevents breakage from a hot, fragile crumb. Wait the full 10 to 15 minutes because cutting too soon can cause the filling to ooze and the slices to collapse. If it sticks when removing, gently run a knife around the edges.