Roasted Tomato Soup

Roasted Tomato Soup is a medium American recipe that serves 2. 560 calories per serving. Recipe by Old's Cool Kevmo on YouTube.

Prep: 35 min | Cook: 1 hr 35 min | Total: 2 hrs 25 min

Cost: $16.10 total, $8.05 per serving

Ingredients

  • 2 lb Vine‑Ripened Tomatoes (quartered)
  • 1 pint Giant Cherry Tomatoes (halved)
  • 1 cup Grape Tomatoes (halved)
  • 1 piece Red Onion (peeled and sliced)
  • 2 heads Garlic (cloves separated, skins left on for roasting)
  • 2 tbsp Olive Oil (extra virgin)
  • 1 tsp Kosher Salt (plus extra pinch at end)
  • 0.5 tsp Black Pepper (freshly ground)
  • 1 tsp Dried Oregano (optional)
  • 1 tsp Dried Thyme (optional)
  • 0.5 tsp Dried Chili Flakes (adjust to taste)
  • 4 cup Chicken Stock (low‑sodium)
  • 0.25 cup Fresh Basil (chopped)
  • 0.5 cup Heavy Cream (room temperature)
  • 1 tbsp Sherry Vinegar (adds acidity)
  • 4 slice Sourdough Bread (thick slices)
  • 2 slice Gouda Cheese (medium aged)
  • 2 slice Cheddar Cheese (sharp)
  • 2 slice Monterey Jack Cheese (mild)
  • 2 tbsp Unsalted Butter (softened)

Instructions

  1. Preheat Oven

    Set the oven to 450°F (230°C) and let it preheat.

    Time: PT10M

    Temperature: 450°F

  2. Prepare Vegetables

    Quarter the vine‑ripened tomatoes, halve the giant cherry tomatoes and grape tomatoes, slice the red onion, and split the garlic heads into cloves, leaving skins on for roasting.

    Time: PT10M

  3. Season and Arrange

    In a large mixing bowl, toss all the vegetables with olive oil, kosher salt, black pepper, dried oregano, dried thyme, and chili flakes. Spread them in a single layer on a baking sheet.

    Time: PT5M

  4. Roast Vegetables

    Place the baking sheet in the preheated oven and roast for 40 minutes, stirring once halfway through, until the tomatoes are deeply browned and the garlic is soft.

    Time: PT40M

    Temperature: 450°F

  5. Transfer to Pot and Add Stock

    Using tongs, move the roasted vegetables to a saucepan. Squeeze the softened roasted garlic cloves into the pot, discard skins, and pour in the chicken stock.

    Time: PT5M

  6. Simmer Soup

    Bring the mixture to a gentle simmer over medium heat and let it cook for 30 minutes, allowing the flavors to meld.

    Time: PT30M

    Temperature: medium

  7. Blend Until Smooth

    Remove the pot from heat and use a stick blender to puree the soup directly in the saucepan until completely smooth.

    Time: PT5M

  8. Add Fresh Herbs and Reduce

    Return the pot to low heat, stir in chopped fresh basil, and let the soup simmer gently for 15 minutes.

    Time: PT15M

    Temperature: low

  9. Finish with Cream and Vinegar

    Stir in the heavy cream, add a pinch of kosher salt, and finish with a splash of sherry vinegar. Turn off the heat.

    Time: PT5M

  10. Assemble Grilled Cheese

    Butter one side of each sourdough slice. On the unbuttered side, layer Gouda, cheddar, and Monterey Jack cheese, then top with another slice, buttered side out.

    Time: PT5M

  11. Cook Grilled Cheese

    Heat a griddle or skillet over medium heat. Cook the sandwich for about 2‑3 minutes per side, until the bread is golden brown and the cheese is fully melted.

    Time: PT5M

    Temperature: medium

  12. Serve

    Ladle the hot soup into bowls, tear the grilled cheese sandwich into bite‑size pieces, and dip into the soup. Enjoy immediately.

    Time: PT0M

Nutrition Facts

Calories
560
Protein
22 g
Carbohydrates
48 g
Fat
32 g
Fiber
6 g

Dietary info: Contains meat (chicken stock), Contains alcohol (sherry vinegar)

Allergens: Dairy, Gluten, Garlic

Last updated: April 18, 2026

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Roasted Tomato Soup

Recipe by Old's Cool Kevmo

A comforting winter meal of silky roasted tomato soup paired with a melty triple‑cheese grilled cheese sandwich on sourdough. The soup is roasted, simmered, blended, and finished with fresh basil, cream, and a splash of sherry vinegar for bright acidity. The sandwich uses Gouda, cheddar, and Monterey Jack for ultimate gooeyness.

MediumAmericanServes 2

Shop all ingredients on Amazon in one click • Printable PDF with shopping checklist

Source Video
30m
Prep
1h 45m
Cook
16m
Cleanup
2h 31m
Total

Cost Breakdown

$16.10
Total cost
$8.05
Per serving

Critical Success Points

  • Roasting tomatoes until deeply caramelized for maximum flavor.
  • Blending the soup to a completely smooth texture.
  • Adding cream and sherry vinegar at the very end to balance richness and acidity.
  • Cooking the grilled cheese on medium heat to melt the triple cheese without burning the sourdough.

Safety Warnings

  • Use oven mitts when handling the hot baking sheet.
  • Be cautious when blending hot soup; vent the blender lid to avoid steam burns.
  • The skillet will be very hot; keep handles turned away from the edge.

Frequently Asked Questions

Everything you need to know about this recipe

Q

What is the cultural significance and history of roasted tomato soup in American comfort food cuisine?

A

Roasted tomato soup became popular in the United States during the mid‑20th century as a hearty, winter‑time comfort dish. Roasting deepens the tomato flavor, turning a simple pantry staple into a rich, velvety soup that pairs perfectly with grilled cheese, a classic American sandwich.

cultural
Q

What are the traditional regional variations of tomato soup in American cuisine?

A

In the Midwest, tomato soup is often thickened with cream and served with a buttery grilled cheese. In the South, cooks may add a dash of hot sauce or smoked paprika. Some New England versions incorporate fresh herbs like basil or thyme, similar to this recipe.

cultural
Q

How is roasted tomato soup traditionally served in American households?

A

It is typically ladled into a deep bowl, garnished with a drizzle of cream or olive oil, and accompanied by a grilled cheese sandwich cut into strips for dipping. A sprinkle of fresh basil or croutons is also common.

cultural
Q

What occasions or celebrations is roasted tomato soup with grilled cheese associated with in American culture?

A

This pairing is a go‑to comfort meal for cold winter evenings, school lunchboxes, and casual family gatherings. It’s also a popular menu item at diners and coffee shops during the colder months.

cultural
Q

What makes this roasted tomato soup special compared to other tomato soups in American cuisine?

A

The soup’s depth comes from roasting a mix of vine‑ripened, cherry, and grape tomatoes, which adds caramelized sweetness. Finishing with fresh basil, cream, and a splash of sherry vinegar creates a balanced richness and bright acidity that sets it apart.

cultural
Q

What are the most common mistakes to avoid when making roasted tomato soup with grilled cheese at home?

A

Common errors include under‑roasting the tomatoes (resulting in a bland soup), over‑blending which can make the soup watery, and cooking the grilled cheese on too high heat, which burns the bread before the cheese melts. Follow the temperature guidelines and watch the bread color closely.

technical
Q

Why does this recipe use sherry vinegar instead of regular white vinegar?

A

Sherry vinegar provides a milder, more complex acidity that complements the roasted tomato sweetness without overwhelming the soup. It adds a subtle depth that plain white vinegar lacks.

technical
Q

Can I make the roasted tomato soup ahead of time and how should I store it?

A

Yes, the soup can be prepared up to 24 hours in advance. Cool it quickly, transfer to an airtight container, and refrigerate. Reheat gently on the stove, adding a splash of stock if it has thickened.

technical
Q

What does the YouTube channel Old's Cool Kevmo specialize in?

A

The YouTube channel Old's Cool Kevmo focuses on approachable, comfort‑food style cooking videos that blend classic American dishes with practical tips for home cooks. The host often showcases seasonal ingredients and simple techniques.

channel
Q

How does the YouTube channel Old's Cool Kevmo's approach to American comfort food differ from other cooking channels?

A

Old's Cool Kevmo emphasizes minimal equipment, clear step‑by‑step narration, and real‑world kitchen hacks, making the recipes feel achievable for everyday cooks. Unlike highly stylized channels, Kevmo keeps the production simple and focuses on flavor fundamentals.

channel

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